(3-{(R)-1-[5'-chloro-3,3'-difluoro-2'-(5-methyl-[1,2,4]oxadiazol-3-yl)-biphenyl-4-yl]-ethylcarbamoyl}-oxetan-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester → 3-Amino-oxetane-3-carboxylic acid {(R)-1-[5'-chloro-3,3'-difluoro-2'-(5-methyl-[1,2,4]oxadiazol-3-yl)-biphenyl-4-yl]-ethyl}-amide

Participants

Reaction Steps

The title compound was prepared in analogy to intermediate 5 synthesizing {(R)-1-[5′-chloro-3,3′-difluoro-2′-(5-methyl-[1,2,4]oxadiazol-3-yl)-biphenyl-4-yl]ethyl}-carbamic acid tert-butyl ester in step A (using 3-(2-bromo-4-chloro-6-fluoro-phenyl)-5-methyl-[1,2,4]oxadiazole (intermediate 10) instead of 5-(2-bromo-4-chloro-6-fluorophenyl)-2-methyl-2H-tetrazole), (R)-1-[5′-chloro-3,3′-difluoro-2′-(5-methyl-[1,2,4]oxadiazol-3-yl)-biphenyl-4-yl]-ethylamine in step B and (3-{(R)-1-[5′-chloro-3,3′-difluoro-2′-(5-methyl-[1,2,4]oxadiazol-3-yl)-biphenyl-4-yl]-ethylcarbamoyl}-oxetan-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester in step C. White foam. MS: 449.1; [M+H]+.

Provenance & Evidence