N-(tert-butoxycarbonyl)glycine → ethyl 2-(2-((tert-butoxycarbonyl)amino)-N-(4-(trifluoromethoxy)benzyl)acetamido)-2-(2,6-dimethoxyphenyl)acetate

Participants

Reaction Steps

A mixture of ethyl 2-(2,6-dimethoxyphenyl)-2-((4-(trifluoromethoxy)benzyl)-amino)acetate (1.121 g; 2.71 mmol), 2-(tert-butoxycarbonylamino)acetic acid (1.187 g; 6.77 mmol), DIPEA (1.752 g; 13.55 mmol), and HATU (2.577 g; 6.77 mmol) in anh. DMF (20 ml) was stirred at rt, under nitrogen, for 18 h. Et2O (20 ml) and water (20 ml) were then added to the reaction mixture, and the separated aq. layer was further extracted with Et2O (3×50 ml). The mixed organic layers were washed with brine (50 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=50/1) afforded ethyl 2-(2-((tert-butoxycarbonyl)amino)-N-(4-(trifluoromethoxy)benzyl)acetamido)-2-(2,6-dimethoxyphenyl)acetate as a yellow oil. LC-MS (conditions D): tR=1.12 min.; [M+H]+: 571.78 g/mol.

Provenance & Evidence