1,2-Dichloroethane → HCID 87662900, compound

Participants

Reaction Conditions

Reaction Steps

A 1-L round bottom flask was charged with 15.5 g (46.5 mmol) of (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]4-(2,4,5-trifluorophenyl)butanoic acid and 160 mL of acetonitrile. To the resultant suspension was added 14.5 g (60.5 mmol) of amine hydrochloride from Step B. The mixture was cooled to 5° C. and 12 g (62.8 mmol) of EDC and 6.9 mL (62.8 mmol) of N-methylmorpholine were added. After 2 h, the reaction was judged to be complete by LC-MS analysis. The mixture was partitioned between 100 mL of water and 160 mL of ethyl acetate. The organic phase was washed sequentially with 100 mL of saturated aqueous sodium bicarbonate solution and 100 mL of brine, dried over sodium sulfate, and concentrated in vacuo. Purification by Biotage flash chromatography (silica gel, 30–60% ethyl acetate/hexane) gave 20.3 g of the title compound as a white foam. LC-MS 419.4 (M+1-BOC).

Provenance & Evidence