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Azetidine‐2‐carboxylic acid derivatives
Author(s) -
Phillips Barry A.,
Cromwell Norman H.
Publication year - 1973
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570100520
Subject(s) - azetidine , chemistry , thionyl chloride , carboxylic acid , triethylamine , chloride , methanol , organic chemistry , hydrochloride
Abstract An improved method for the preparation of DL ‐azetidine‐2‐carboxylic acid is reported. The reaction of thionyl chloride with azetidine‐2‐carboxylic acid in methanol gave rise to 2‐carbomethoxyazetidine hydrochloride, which upon treatment with triethylamine yielded 2‐carbomethoxyazetidine. 2‐Carbomethoxyazetidine proved to be unstable and upon standing formed azetidine‐2‐carboxylic acid anhydride. The nmr and ir spectra of 2‐carbomethoxyazetidine are discussed in terms of its conformation. The conversion of azetidine‐2‐carboxylic acid to azetidine‐2‐carboxamide is also described.