Diisopropylethylamine → HCID 69026060, compound

Participants

Reaction Steps

A mixture of 363 mg (0.9 mmol) of (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]4-(2-benzyloxy-5-fluorophenyl)butanoic acid, 72 mg (0.3 mmol) of 2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine hydrochloride, 0.174 mL (1.0 mmol) of diisopropylethylamine, 136 mg (1.0 mmol) of 1-hydroxy-7-azabenzotriazole (HOAT) and 380 mg (1.0 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) in 5 mL of dichloromethane was stirred under an atmosphere of nitrogen overnight. The reaction mixture was diluted with 100 mL of ethyl acetate, washed sequentially with 5% hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine, dried over magnesium sulfate, and concentrated. Purification by preparative TLC (silica gel, 70% ethyl acetate/hexane) gave 152 mg (86%) of the title compound.

Provenance & Evidence