Methyl 2-bromopropionate → HCID 66652762, compound

Participants

Reaction Steps

Methyl N-[1-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-alaninate was prepared following the general procedure 11 starting from 1-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethanamine, hydrochloride salt (Example 23, step 2) and methyl 2-bromopropionate. The resulting pair of two diastereomers was separated by flash chromatography (heptane/EtOAc gradient from 95:5 up to 85:15), affording methyl N-[(1S)-1-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-D-alaninate and methyl N-[(1R)-1-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-L-alaninate (75 mg, 27%) as one fraction and methyl N-[(1S)-1-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-L-alaninate and methyl N-[(1R)-1-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-D-alaninate (50 mg, 18%) as a second fraction.

Provenance & Evidence