The synthesis of DL-3,3-Difluoroglutamic acid from a 3-oxoprolinol derivative

DL-3,3-Difluoroglutamic acid was synthesized from a masked 3-hydroxyprolinol, 6-hydroxy-1-aza-3-oxabicyclo[3.3.0]octan-2-one, in eight steps. The described synthetic route expands the utility of fluoroproline derivatives as precursors of fluoroglutamic acids. A practical synthesis of 3,3-difluoroglu...

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Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 31; pp. 4917 - 4920
Main Authors Hart, Barry P., Coward, James K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.07.1993
Elsevier
Subjects
Aliphatic compounds
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
OXIDATION
METHOTREXATE
Diethylaminosulfur trifluoride
α-Aminoacid
Aliphatic compound
Saturated compound
Bicyclic compound
Racemate
Dicarboxylic acid
Fluorine Organic compounds
Organic carbamate
Oxygen nitrogen heterocycle
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Summary:DL-3,3-Difluoroglutamic acid was synthesized from a masked 3-hydroxyprolinol, 6-hydroxy-1-aza-3-oxabicyclo[3.3.0]octan-2-one, in eight steps. The described synthetic route expands the utility of fluoroproline derivatives as precursors of fluoroglutamic acids. A practical synthesis of 3,3-difluoroglutamic from 6-hydroxy-1-aza-3- oxabicyclo[3.3.0]octan-2-one utilizes 3,3-difluoroprolinol and 3,3-difluoropyroglutamate derivatives as critical intermediates.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)74045-7