N-Methyl-4-anisidine → HCID 90289952, compound

Participants

Reaction Steps

(S)-2-(tert-Butoxycarbonylamino)-3-(3-bromophenyl)propanoic acid (660 mg, 1.92 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 803 mg, 2.1 mmol) and DIPEA (0.43 ml, 2.5 mmol) were dissolved in DMF (10 ml) and treated with 4-methoxy-N-methylaniline (316 g, 2.3 mmol). The mixture was stirred vigorously overnight. The mixture was diluted with EtOAc (100 ml) and washed with brine (2×50 ml). The organic layer was dried over Na2SO4, filtered and concentrated. The oily crude product was introduced to a silica gel loading column and purified by column chromatography (15-38% EtOAc/hexanes) to provide the desired product (770 mg, 1.66 mmol), 86.5%. MS (m/z) 463 [M+H]+.

Provenance & Evidence