A Highly Convergent Synthesis of a Fibrinogen Receptor Antagonist
A practical multikilogram synthesis of 2(S)-[(p-toluenesulfonyl)amino]-3-[[[5,6,7,8-tetrahydro-4-oxo-5-[2-(piperidin-4-yl)ethyl]-4H-pyrazolo[1,5-a][1,4]diazepin-2-yl]carbonyl]amino]propionic acid pentahydrate (1), an oral fibrinogen receptor antagonist, is described. The nine-step convergent process...
Saved in:
| Published in | Journal of organic chemistry Vol. 64; no. 21; pp. 7751 - 7755 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
15.10.1999
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | A practical multikilogram synthesis of 2(S)-[(p-toluenesulfonyl)amino]-3-[[[5,6,7,8-tetrahydro-4-oxo-5-[2-(piperidin-4-yl)ethyl]-4H-pyrazolo[1,5-a][1,4]diazepin-2-yl]carbonyl]amino]propionic acid pentahydrate (1), an oral fibrinogen receptor antagonist, is described. The nine-step convergent process, which afforded 1 in 37% overall yield, included pyrazole 5a and N-tosylaminoalanine 16 as key fragments. Pyrazole 5a was obtained from pyrazole-3,5-dicarboxylic acid by esterification with MeOH, alkylation/cyclization with 3-bromopropylamine, and Michael addition with 4-vinylpyridine. N-Tosylaminoalanine 16 was prepared by tosylation of asparagine, Hofmann reaction, and benzyl esterification. Saponification of pyrazole 5a, coupling of the acid with N-tosylaminoalanine 16, and Pd-catalyzed hydrogenolysis and pyridine reduction completed the synthesis. |
|---|---|
| AbstractList | A practical multikilogram synthesis of 2(S)-[(p-toluenesulfonyl)amino]-3-[[[5,6,7,8-tetrahydro-4-oxo-5-[2-(piperidin-4-yl)ethyl]-4H-pyrazolo[1,5-a][1,4]diazepin-2-yl]carbonyl]amino]propionic acid pentahydrate (1), an oral fibrinogen receptor antagonist, is described. The nine-step convergent process, which afforded 1 in 37% overall yield, included pyrazole 5a and N-tosylaminoalanine 16 as key fragments. Pyrazole 5a was obtained from pyrazole-3,5-dicarboxylic acid by esterification with MeOH, alkylation/cyclization with 3-bromopropylamine, and Michael addition with 4-vinylpyridine. N-Tosylaminoalanine 16 was prepared by tosylation of asparagine, Hofmann reaction, and benzyl esterification. Saponification of pyrazole 5a, coupling of the acid with N-tosylaminoalanine 16, and Pd-catalyzed hydrogenolysis and pyridine reduction completed the synthesis. |
| Author | Cvetovich, Raymond J Pipik, Brenda Grabowski, Edward J. J Hartner, Frederick W Amato, Joseph S Tsay, Fuh-Rong Reider, Paul J |
| Author_xml | – sequence: 1 givenname: Frederick W surname: Hartner fullname: Hartner, Frederick W – sequence: 2 givenname: Raymond J surname: Cvetovich fullname: Cvetovich, Raymond J – sequence: 3 givenname: Fuh-Rong surname: Tsay fullname: Tsay, Fuh-Rong – sequence: 4 givenname: Joseph S surname: Amato fullname: Amato, Joseph S – sequence: 5 givenname: Brenda surname: Pipik fullname: Pipik, Brenda – sequence: 6 givenname: Edward J. J surname: Grabowski fullname: Grabowski, Edward J. J – sequence: 7 givenname: Paul J surname: Reider fullname: Reider, Paul J |
| BookMark | eNqNkEFLAzEQhYNUsK0e_Ad78SCymk026eZYFmuFimIriJclm51tU2tSklTtv3eXlZ48OJcZmO8N894A9Yw1gNB5gq8TTJKbtRUC8zQNR6ifMIJjLnDaQ32MCYkp4fQEDbxf46YYY300HkdTvVxt9lFuzSe4JZgQzfcmrMBrH9k6ktFEl04b26yiZ1CwDdZFYxPk0hrtwyk6ruXGw9lvH6KXye0in8azx7v7fDyLJREsxKwSoMoaSqJYUlJJ07rOmOAgKix4lQqsJOEEeMUIY1VFGa2k5IJyPAJFFB2iy-6uctZ7B3WxdfpDun2R4KL1Xhy8N2zWsV9Q2torDUbBgW_NZ5RkmLWTyHWQQVuT251ppVf_lzZ03NFNEPB9wKR7L_iIjlixeJoXi2yKszf-Wjw0_EXHS-Wbf3fONJH9YeAH9HKKDA |
| CitedBy_id | crossref_primary_10_3987_COM_06_10803 crossref_primary_10_1016_S0040_4039_03_01417_5 crossref_primary_10_1055_a_2016_4337 crossref_primary_10_1016_j_tet_2006_06_002 crossref_primary_10_1007_s11030_020_10161_8 crossref_primary_10_1016_j_ica_2022_120956 crossref_primary_10_1021_op500305s |
| Cites_doi | 10.1016/0960-894X(95)00057-Z 10.1021/jm9608117 10.1021/jo00263a032 10.1021/ja01597a073 10.1021/jo01155a008 10.1135/cccc19591993 10.1021/jm960626t 10.1021/jo980799l 10.1021/ma60017a619 10.1021/ja01625a080 10.1021/jo951214f |
| ContentType | Journal Article |
| Copyright | Copyright © 1999 American Chemical Society |
| Copyright_xml | – notice: Copyright © 1999 American Chemical Society |
| DBID | BSCLL 1KM 1KN BLEPL DTL FGRAT AAYXX CITATION |
| DOI | 10.1021/jo990644t |
| DatabaseName | Istex Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 1999 CrossRef |
| DatabaseTitle | Web of Science CrossRef |
| DatabaseTitleList | Web of Science |
| Database_xml | – sequence: 1 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1520-6904 |
| EndPage | 7755 |
| ExternalDocumentID | 10_1021_jo990644t 000083280500009 ark_67375_TPS_T8H08Z6X_M a907176250 |
| GroupedDBID | - .K2 186 29L 3EH 53G 55A 5RE 5VS 7~N 85S AABXI ABDEX ABFLS ABMVS ABPPZ ABPTK ABUCX ABUFD ACCAO ACGFS ACJ ACNCT ACS ACTDY ADKFC AEESW AENEX AETEA AFDAS AFEFF AFMIJ AIDAL ALMA_UNASSIGNED_HOLDINGS ANTXH AQSVZ BAANH CJ0 CS3 D0L DU5 DZ EBS ED ED~ EJD F20 F5P GJ GNL IH9 IHE JG JG~ K2 LG6 MVM NHB OHM OHT P2P PZZ ROL RXW TAE TAF TN5 UI2 UMD UNC UPT UQL VF5 VG9 VH1 VQA W1F WH7 X X7L XFK YQJ YXE YZZ ZCG ZE2 ZGI ZY4 --- -DZ -~X .GJ 6TJ AAHBH AAYOK ABJNI ABQRX ACBEA ACGFO ADHLV AGXLV AHGAQ AI. BSCLL CUPRZ GGK IH2 XOL XSW XXG YQT YYP ZCA 1KM 1KN BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED AAYXX ACRPL ADNMO CITATION |
| ID | FETCH-LOGICAL-a295t-5d9ecbfeb2c51b3a34ff8596e9d096d490ca262e6d5255dd353daa693607ec2c3 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 8 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000083280500009 |
| ISSN | 0022-3263 |
| IngestDate | Fri Dec 06 03:18:49 EST 2024 Sun Sep 29 09:22:40 EDT 2024 Fri Dec 13 17:53:36 EST 2024 Wed Oct 30 09:20:12 EDT 2024 Thu Aug 27 13:42:51 EDT 2020 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 21 |
| Keywords | PEPTIDE MIMETICS DESIGN GLYCOPROTEIN IIB/IIIA INHIBITORS 4-VINYLPYRIDINE |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a295t-5d9ecbfeb2c51b3a34ff8596e9d096d490ca262e6d5255dd353daa693607ec2c3 |
| Notes | ark:/67375/TPS-T8H08Z6X-M istex:12AF72D10B259D55AB2BD80220864F7AA843F3F8 |
| PageCount | 5 |
| ParticipantIDs | crossref_primary_10_1021_jo990644t webofscience_primary_000083280500009CitationCount istex_primary_ark_67375_TPS_T8H08Z6X_M webofscience_primary_000083280500009 acs_journals_10_1021_jo990644t |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N ACJ VG9 W1F ANTXH ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 |
| PublicationCentury | 1900 |
| PublicationDate | 1999-10-15 |
| PublicationDateYYYYMMDD | 1999-10-15 |
| PublicationDate_xml | – month: 10 year: 1999 text: 1999-10-15 day: 15 |
| PublicationDecade | 1990 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON |
| PublicationTitle | Journal of organic chemistry |
| PublicationTitleAbbrev | J ORG CHEM |
| PublicationTitleAlternate | J. Org. Chem |
| PublicationYear | 1999 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | ZAORAL, M (WOS:A1959WV84600034) 1959; 24 BRADY, LE (WOS:A19616262B00018) 1961; 26 Hutchinson, JH (WOS:A1996VR62400010) 1996; 39 OJIMA, I (WOS:A1995RB11800001) 1995; 3 KIRCHNER, FK (WOS:A1949UQ12100008) 1949; 14 MAGNUS, G (WOS:A1956WB83900073) 1956; 78 FIFE, WK (WOS:A1990ED04500019) 1990; 55 Askew, BC (WOS:A1997XC90100005) 1997; 40 TAWIL, BF (WOS:A1992HT78100006) 1992; 48 NICHOLS, AJ (WOS:A1994BA81Y00013) 1994 GRAY, AP (WOS:A1957WB81300049) 1957; 79 LEE, HH (WOS:A1989R976700032) 1989; 54 ASKEW, BC (WOS:A1995QM74100011) 1995; 5 SCHROR, K (WOS:A1995RG11400002) 1995; 50 Klein, SI (WOS:A1996UU38100023) 1996; 6 Stilz, HU (WOS:A1996VV96500010) 1996; 105 Cook, Nigel S. (BCI:BCI199497228289) 1994; 19 Chung, JYL (WOS:A1996TQ14600035) 1996; 61 SALAMONE, JC (WOS:A1970H510300045) 1970; 3 Wityak, J (WOS:A1997WB84900009) 1997; 40 REICH, HE (WOS:A1955WB86700080) 1955; 77 Amato, JS (WOS:000077498400061) 1998; 63 Askew B. C. (jo990644tb00007/jo990644tb00007_1) 1995; 5 Magnus G. (jo990644tb00010/jo990644tb00010_1) 1956; 78 Salamone J. C. (jo990644tb00011/jo990644tb00011_1) 1970; 3 Zaoral M. (jo990644tb00012/jo990644tb00012_1) 1959; 24 Wityak J. (jo990644tb00002/jo990644tb00002_1) 1997; 40 Amato J. S. (jo990644tb00013/jo990644tb00013_1) 1998; 63 jo990644tb00001/jo990644tb00001_1 Reich H. E. (jo990644tb00006/jo990644tb00006_1) 1955; 77 Kirchner F. K. (jo990644tb00009/jo990644tb00009_1) 1949; 14 Askew B. C. (jo990644tb00003/jo990644tb00003_1) 1997; 40 Lee H. H. (jo990644tb00005/jo990644tb00005_1) 1989; 54 Chung J. Y. L. (jo990644tb00004/jo990644tb00004_1) 1996; 61 |
| References_xml | – volume: 40 start-page: 50 year: 1997 ident: WOS:A1997WB84900009 article-title: Discovery of potent isoxazoline glycoprotein IIb/IIIa receptor antagonists publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Wityak, J – volume: 55 start-page: 5610 year: 1990 ident: WOS:A1990ED04500019 article-title: A GENERAL-SYNTHESIS OF 1-ALKYL-4-VINYLPYRIDINIUM IONS - ALKYLATION OF 4-VINYLPYRIDINE WITH PRIMARY ALKYL TRIFLATES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: FIFE, WK – volume: 105 start-page: 711 year: 1996 ident: WOS:A1996VV96500010 article-title: From peptides to heterocyclic peptide mimetics - Design and synthesis of an orally active fibrinogen receptor antagonist for the prevention of thrombosis publication-title: BULLETIN DES SOCIETES CHIMIQUES BELGES contributor: fullname: Stilz, HU – volume: 19 start-page: 135 year: 1994 ident: BCI:BCI199497228289 article-title: Platelet glycoprotein IIb/IIIa antagonists publication-title: Drugs of the Future contributor: fullname: Cook, Nigel S. – volume: 50 start-page: 7 year: 1995 ident: WOS:A1995RG11400002 article-title: ANTIPLATELET DRUGS - A COMPARATIVE REVIEW publication-title: DRUGS contributor: fullname: SCHROR, K – volume: 26 start-page: 4757 year: 1961 ident: WOS:A19616262B00018 article-title: SOME AMINOETHYLPIPERIDINES AND -PYRIDINES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BRADY, LE – volume: 54 start-page: 428 year: 1989 ident: WOS:A1989R976700032 article-title: SYNTHESIS AND CHARACTERIZATION OF MASKED AMINOPYRAZOLECARBOXYLIC ACID SYNTHONS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: LEE, HH – volume: 5 start-page: 475 year: 1995 ident: WOS:A1995QM74100011 article-title: NONPEPTIDE GLYCOPROTEIN IIB/IIIA INHIBITORS .6. DESIGN AND SYNTHESIS OF RIGID, CENTRALLY CONSTRAINED NONPEPTIDE FIBRINOGEN RECEPTOR ANTAGONISTS publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS contributor: fullname: ASKEW, BC – volume: 3 start-page: 337 year: 1995 ident: WOS:A1995RB11800001 article-title: ANTITHROMBOTIC AGENTS - FROM RGD TO PEPTIDE MIMETICS publication-title: BIOORGANIC & MEDICINAL CHEMISTRY contributor: fullname: OJIMA, I – volume: 24 start-page: 1993 year: 1959 ident: WOS:A1959WV84600034 article-title: AMINO-ACIDS AND PEPTIDES .25. DEHYDRATION OF DERIVATIVES OF ASPARAGINE AND GLUTAMINE - A NEW ROUTE TO ALPHA,GAMMA-DIAMINOBUTYRIC ACID, ORNITHINE, AND ARGININE publication-title: COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS contributor: fullname: ZAORAL, M – volume: 6 start-page: 1403 year: 1996 ident: WOS:A1996UU38100023 article-title: Non-peptide fibrinogen receptor antagonists based upon a 4-substituted piperidine scaffold publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS contributor: fullname: Klein, SI – volume: 14 start-page: 388 year: 1949 ident: WOS:A1949UQ12100008 article-title: THE USE OF DIAZO COMPOUNDS IN THE PREPARATION OF SOME BENZYLPENICILLIN ESTERS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: KIRCHNER, FK – volume: 39 start-page: 4583 year: 1996 ident: WOS:A1996VR62400010 article-title: Non-peptide glycoprotein IIb/IIIa antagonists .2. Design and in vivo evaluation of 3,4-dihydro-1(1H)-isoquinolinone-based antagonists and ethyl ester prodrugs publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Hutchinson, JH – volume: 77 start-page: 5434 year: 1955 ident: WOS:A1955WB86700080 article-title: THE PYRIDYLETHYLATION OF ACTIVE HYDROGEN COMPOUNDS .4. THE ACID-CATALYZED PYRIDYLETHYLATION OF PRIMARY AMINES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: REICH, HE – volume: 63 start-page: 9533 year: 1998 ident: WOS:000077498400061 article-title: Development of the Hofmann rearrangement of N alpha-tosylasparagine through calorimetric and NMR analysis publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Amato, JS – volume: 40 start-page: 1779 year: 1997 ident: WOS:A1997XC90100005 article-title: Non-peptide glycoprotein IIb/IIIa inhibitors .17. Design and synthesis of orally active, long-acting non-peptide fibrinogen receptor antagonists publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Askew, BC – volume: 79 start-page: 3805 year: 1957 ident: WOS:A1957WB81300049 article-title: BIS-AMMONIUM SALTS - UNSYMMETRIC DERIVATIVES OF SUBSTITUTED PYRIDINE BASES THAT ARE POTENT AND SELECTIVE HYPOTENSIVE AGENTS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: GRAY, AP – volume: 61 start-page: 215 year: 1996 ident: WOS:A1996TQ14600035 article-title: Highly efficient synthesis of fibrinogen receptor antagonist L-734,217 via a novel chemoselective silyl-mediated conjugate addition of delta-lactams to 4-vinylpyridine publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Chung, JYL – volume: 48 start-page: 3775 year: 1992 ident: WOS:A1992HT78100006 article-title: SYNTHESIS OF THE SPERMIDINE ALKALOID (+/-)-N(1)-ACETYL-N(1)-DEOXYMAYFOLINE publication-title: TETRAHEDRON contributor: fullname: TAWIL, BF – volume: 78 start-page: 4127 year: 1956 ident: WOS:A1956WB83900073 article-title: THE PYRIDYLETHYLATION OF ACTIVE HYDROGEN COMPOUNDS .5. THE REACTION OF AMMONIA, CERTAIN AMINES, AMIDES AND NITRILES WITH 2-VINYLPYRIDINE AND 4-VINYLPYRIDINE AND 2-METHYL-5-VINYLPYRIDINE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MAGNUS, G – volume: 3 start-page: 707 year: 1970 ident: WOS:A1970H510300045 article-title: POLYMERIZATION OF 4-VINYLPYRIDINIUM SALTA .2. HYDROGEN-TRANSFER POLYMERIZATION publication-title: MACROMOLECULES contributor: fullname: SALAMONE, JC – start-page: 213 year: 1994 ident: WOS:A1994BA81Y00013 article-title: GPIIB/IIIA ANTAGONISTS AS NOVEL ANTITHROMBOTIC DRUGS - POTENTIAL THERAPEUTIC APPLICATIONS publication-title: CELLULAR ADHESION contributor: fullname: NICHOLS, AJ – volume: 5 start-page: 475 year: 1995 ident: jo990644tb00007/jo990644tb00007_1 publication-title: J. Bioorg. Med. Chem. Lett. doi: 10.1016/0960-894X(95)00057-Z contributor: fullname: Askew B. C. – volume: 40 start-page: 1779 year: 1997 ident: jo990644tb00003/jo990644tb00003_1 publication-title: J. Med. Chem. doi: 10.1021/jm9608117 contributor: fullname: Askew B. C. – volume: 54 start-page: 428 year: 1989 ident: jo990644tb00005/jo990644tb00005_1 publication-title: J. Org. Chem. doi: 10.1021/jo00263a032 contributor: fullname: Lee H. H. – volume: 78 start-page: 4127 year: 1956 ident: jo990644tb00010/jo990644tb00010_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01597a073 contributor: fullname: Magnus G. – volume: 14 start-page: 388 year: 1949 ident: jo990644tb00009/jo990644tb00009_1 publication-title: J. Org. Chem. doi: 10.1021/jo01155a008 contributor: fullname: Kirchner F. K. – volume: 24 start-page: 1993 year: 1959 ident: jo990644tb00012/jo990644tb00012_1 publication-title: Collect. Czech. Chem. Commun. doi: 10.1135/cccc19591993 contributor: fullname: Zaoral M. – volume: 40 start-page: 50 year: 1997 ident: jo990644tb00002/jo990644tb00002_1 publication-title: J. Med. Chem. doi: 10.1021/jm960626t contributor: fullname: Wityak J. – ident: jo990644tb00001/jo990644tb00001_1 – volume: 63 start-page: 9533 year: 1998 ident: jo990644tb00013/jo990644tb00013_1 publication-title: J. Org. Chem. doi: 10.1021/jo980799l contributor: fullname: Amato J. S. – volume: 3 start-page: 707 year: 1970 ident: jo990644tb00011/jo990644tb00011_1 publication-title: Macromolecules doi: 10.1021/ma60017a619 contributor: fullname: Salamone J. C. – volume: 77 start-page: 5434 year: 1955 ident: jo990644tb00006/jo990644tb00006_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01625a080 contributor: fullname: Reich H. E. – volume: 61 start-page: 215 year: 1996 ident: jo990644tb00004/jo990644tb00004_1 publication-title: J. Org. Chem. doi: 10.1021/jo951214f contributor: fullname: Chung J. Y. L. |
| SSID | ssj0000555 |
| Score | 1.67382 |
| Snippet | A practical multikilogram synthesis of... |
| Source | Web of Science |
| SourceID | crossref webofscience istex acs |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 7751 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | A Highly Convergent Synthesis of a Fibrinogen Receptor Antagonist |
| URI | http://dx.doi.org/10.1021/jo990644t https://api.istex.fr/ark:/67375/TPS-T8H08Z6X-M/fulltext.pdf http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000083280500009 |
| Volume | 64 |
| WOS | 000083280500009 |
| WOSCitedRecordID | wos000083280500009 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LSwMxEB60HvTiW6yPErR4W-0mm3RzLKulCIrQCsXLks0moJVtsStYf72TbbcqPs-ZwO7kMd_HzHwBqItQa6kl85QR2guaCfdcdgnPlfWtEUloCyHtq2vRuQ0u-7y_AMc_ZPCpf_YwxAsTo3a-CEu0ibTb4Z-o-37dcs7nkuBUsFI-6ONUF3r0-FPoWXJefPk23BShpb0G52WDzrSiZHD6nCen-vWrXuNvX70OqzNoSVrTvbABCybbhOWofNFtC1ot4so6HickcrXmru0yJ91JhhhwfD8mQ0sUabsWgGyIQwQRpRkhJSetzKWunMTuNty2L3pRx5s9oeApKnnu8VQanVikz5r7CVMssDbkUhiZIndJA9nQigpqRMqRW6Qp4yxVSkgmGk2jqWY7UMmGmdkFoq2ROGgTzU0QKhsiVEqdPho3OJWJKtTQx_HsCIzjIrtNkV2UnqjCUen-eDSV0vjO6KRYmLmFehq42rMmj3s33bgXdhrhnejHV1Wof1y5uX0BghkNG7yAv1Xw_2MWzQTRnRBAvvfXn-zDSqHe4Apb-AFU8qdnc4jYJE9qxd58AzmL3Eo |
| link.rule.ids | 314,780,784,2765,27076,27924,27925,56738,56788 |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3dT9swED-x8sBeNgZMdIPOQoi3QBvn3Pixiqi6QRFSi1TxEjmOLUGntGqCNPbX7-ym5UNI49nn6HL-uN_pzr8DOBax1lJLHigjdBB1MwxcdonOle1YI7LYeiLt4ZUY3ES_JjipaXLcWxhSoqQvlT6J_8Qu0Dm7n9G9Sc67-gCb6FpVOhiUjJ5uXURcM4OHgq9YhJ5PdR5Ily880KYz5p83vY73MP3Py1ZFXjdfWDI9faiyU_33FW3j-5Tfhk810GS95c74Ahum2IGtZNXfbRd6PeaKPH4_ssRVnrtHmBUbPRaECMu7ks0sU6zvHgQUMxpihC_NnAJ01itcIssR7u7BTf98nAyCuqFCoEKJVYC5NDqzFExr7GRc8cjaGKUwMqdIJo9kW6tQhEbkSJFGnnPkuVJCctHuGh1q_hUaxaww-8C0NZIGbabRRLGyMQGn3LGloaGpXDShRYZI6wNRpj7XHVKssbJEE45Wq5DOl8Qabwmd-PVZS6jF1FWidTEdX4_ScTxox7dikg6bcPx8AdfyHhLzMG6jB8NN6LxHLKnp0R0tQPXtf3_yA7YG4-Flevnz6uI7fPS8Dq7kBQ-gUS0ezCGhlipr-e36D4w_5Lc |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1ZTxsxEB4VkICXHhwiPcCqEG8LyXrHWT-uto3SUg4pQYp4WXl9SDTVJmIXqfTXd2w2Ka2QyrPHlq-Z-UYz_gxwKFKtpZY8UlboKOmXGPnsEumV6zkrytQFIu2zczG8Sr5OcNIGiv4tDE2ippHqkMT3Wj03rmUY6J18n5HtJAferMAakpX1JVxZPvpjeRFxyQ4eC75gEnrc1XshXf_lhdb8hv580vMELzN4BRfL-YXikunxXVMe61__UDc-fwGv4WULOFn2cEPewAtbbcFGvvjnbRuyjPlijx_3LPcV6P4xZsNG9xUhw_qmZjPHFBv4hwHVjJoY4Uw7p0CdZZVPaHni3R24Gnwe58Oo_VghUrHEJkIjrS4dBdUaeyVXPHEuRSmsNBTRmER2tYpFbIVBijiM4ciNUkJy0e1bHWu-C6vVrLJ7wLSzkhpdqdEmqXIpASjjWdPQUlcuOrBPm1G0ilEXIecdU8yx2IkOfFycRDF_INh4SugonNFSQt1OfUVaH4vx5agYp8Nuei0mxVkHDh8f4lI-QGMep10MoLgDveeI5S1NuqcHaN7-byUHsH75aVB8-3J--g42A72Dr3zB97Da3N7ZDwRemnI_3NjfIMDnOg |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=A+Highly+Convergent+Synthesis+of+a+Fibrinogen+Receptor+Antagonist&rft.jtitle=Journal+of+organic+chemistry&rft.au=HARTNER%2C+Frederick+W.&rft.au=CVETOVICH%2C+Raymond+J.&rft.au=TSAY%2C+Fuh-Rong&rft.au=AMATO%2C+Joseph+S.&rft.date=1999-10-15&rft.pub=American+Chemical+Society&rft.issn=0022-3263&rft.eissn=1520-6904&rft.volume=64&rft.issue=21&rft.spage=7751&rft.epage=7755&rft_id=info:doi/10.1021%2Fjo990644t&rft.externalDBID=n%2Fa&rft.externalDocID=ark_67375_TPS_T8H08Z6X_M |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0022-3263&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0022-3263&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0022-3263&client=summon |