A Practical and Diastereoselective Synthesis of Angiotensin Converting Enzyme Inhibitors

The diastereoselective synthesis of a series of potent angiotensin converting enzyme (ACE) inhibitors is described. The optically active intermediate, N-carbamyl (R)-2-amino-4-phenylbutyric acid (2) leading to (R)-2-halogeno or (R)-2-hydroxy-4-phenylbutyric acid was prepared by asymmetric hydrolysis...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 37; no. 2; pp. 280 - 283
Main Authors IWASAKI, Genji, KIMURA, Rieko, NUMAO, Naganori, KONDO, Kiyosi
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 1989
Pharmaceutical Soc Japan
Maruzen
Japan Science and Technology Agency
Subjects
(R)-2-halogeno-4-phenylbutyric acid
ACE inhibitor
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
enalapril
enzymatic hydrolysis
Exact sciences and technology
hydantoinase
Life Sciences & Biomedicine
lisinopril
N-carbamyl (R)-2-amino-4-phenylbutyric acid
Noncondensed benzenic compounds
Organic chemistry
Pharmacology & Pharmacy
Physical Sciences
Preparations and properties
Science & Technology
α-Aminoacid
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Summary:The diastereoselective synthesis of a series of potent angiotensin converting enzyme (ACE) inhibitors is described. The optically active intermediate, N-carbamyl (R)-2-amino-4-phenylbutyric acid (2) leading to (R)-2-halogeno or (R)-2-hydroxy-4-phenylbutyric acid was prepared by asymmetric hydrolysis of DL-5-phenethylhydantoin (1) by microbial hydantoinase. The halogenoester was subjected to SN2 reaction with L-amino acid derivatives to afford N-substituted amino acids, which were easily converted to ACE inhibitors or intermediates by deprotection.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.37.280