(1R,3S,5S)-2-[2-(3-acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetyl]-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamide → (2S,4R)-1-[2-(3-Acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetyl]-4-fluoro-4-methyl-pyrrolidine-2-carboxylic acid [(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethyl]-amide

Participants

Reaction Steps

The title compound was prepared in 2 steps according to the procedure described for the preparation of Example 610 (1R,3S,5S)-2-[2-(3-acetyl-pyrrolo[2,3-b]pyridin-1-yl)-acetyl]-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamide from (2S,4R)-2-[(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethylcarbamoyl]-4-fluoro-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared using similar protocols as described in Scheme B9). White powder. TLC, Rf (CH2/Cl2/EtOAc 9:1)=0.60; MS (UPLC/MS): 519.3/521.3 [M+H]+, 563.3/565.3 [M+HCOO]−; tR (HPLC conditions a): 2.96 min.

Provenance & Evidence