4-Methylmorpholine → (S)-4-[[(S)-2-(3-Chloro-4-trifluoromethyl-phenylamino)-propionyl]-(2,2-dimethoxy-ethyl)-amino]-3-hydroxy-butyric acid methyl ester

Participants

Reaction Steps

To a solution of 0.915 g (3.4 mmol) of (S)-2-(3-chloro-4-trifluoromethyl-phenylamino)-propionic acid (26% ee) (intermediate 32) and 0.394 ml (3.6 mmol) of 4-methylmorpholine in 10.0 ml of DMF, was added at 0° C. 1.86 g (4.9 mmol) of HATU, followed after 30 min by 1.20 g (3.3 mmol) of (S)-4-(2,2-dimethoxy-ethylamino)-3-hydroxy-butyric acid methyl ester in 6.5 ml of DMF. The solution was stirred and warmed up over night. The reaction was poured on aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous 10% KHSO4, saturated NaHCO3, 10% NaCl and dried over Na2SO4 to yield 1.91 g (62%) of the titled compound as light brown oil. MS: 469.14 (MH+).

Provenance & Evidence