N-Methyl-4-anisidine → (S)-tert-butyl 3-(3-iodophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Participants

Reaction Steps

(S)-2-(tert-Butoxycarbonylamino)-3-(3-iodophenyl)propanoic acid (3.8 g, 9.65 mmol), 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 4.4 g, 11.6 mmol) and DIPEA (2.5 ml, 14.5 mmol) were dissolved in DMF (10 ml) and treated with 4-methoxy-N-methylaniline (1.59 g, 11.6 mmol). The mixture was stirred vigorously overnight at room temperature. 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 (4.63 g, 9.07 mmol), 94%. MS (m/z) 511 [M+H]+.

Provenance & Evidence