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

• Published in: Tetrahedron letters Vol. 34; no. 31; pp. 4917 - 4920
• Main Authors: Hart, Barry P., Coward, James K.
• Format: Journal Article
• Language: English
• 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

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...