Sodium Hydroxide → HCID 68283741, compound

Participants

Reaction Steps

were obtained using the same protocols as described in Scheme B28 steps D and E for the preparation of (1R,3S,5S) and (1S,3S,5R)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester starting from (1R,3S,5S) and (1S,3S,5R)-5-methoxymethyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester. NaOH was replaced by LiOH.H2O in step D. The diastereoisomers were separated by flash column chromatography on silica gel (c-hexane/EtOAc 1:1 to EtOAc) to give (1S,3S,5R)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-5-methoxymethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester as a colorless oil: TLC, Rf (c-hexane/EtOAc 1:1)=0.50; MS (UPLC/MS): 413.3/415.2 [M+H]+, 457.3/459.3 [M+HCOO]−; tR (HPLC conditions a): 3.74 min and (1R,3S,5S)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-5-methoxymethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester as a colorless oil: TLC, Rf (c-hexane/EtOAc 1:1)=0.30; MS (UPLC/MS): 413.2/415.3 [M+H]+, 457.3/459.3 [M+HCOO]−; tR (HPLC conditions a): 3.57 min.

Provenance & Evidence