Methyl 2-bromopropionate → HCID 66652902, compound

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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 and methyl 2-bromopropionate. The resulting pair of two diastereomers could be 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 (90 mg, 33%) as a first 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 (85 mg, 31%) as second fraction.

Provenance & Evidence