1,2-Dichloroethane → N-(2-Benzyloxy-1-carbamoyl-ethyl)-2-cyclohexylmethyl-4-morpholin-4-yl-oxo-butyramide

Participants

Reaction Conditions

Reaction Steps

(R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid (0.20 g, 0.71 mmol) was dissolved in 6 mL of DMF and cooled to 0° C. with an ice-water bath. EDC (0.18 g, 0.92 mmol) and 1-hydroxybenzotriazole (0.12 g, 0.92 mmol) were added and stirring, under argon, continued for 25 min. To the cold solution was added the HCl salt of O-benzyl-L-serineamide (0.16 g, 0.71 mmol), followed by addition of N-methylmorpholine (0.23 mL, 2.10 mmol) and stirring was continued overnight (16 h). The solution was diluted with 100 mL of EtOAc and washed with a 1.0 M solution of HCl (3×10 mL), a saturated solution of NaHCO3 (3×10 mL), water (100 mL) then with brine (100 mL). The organic layer was dried over MgSO4, filtered and concentrated by rotary evaporation to give (0.34 g, 106%) of the crude product which was chromatographed (SiO2, 2% MeOH in EtOAc) to give N-(2-Benzyloxy-1-carbamoyl-ethyl)-2-cyclohexylmethyl-4-morpholin-4-yl-oxo-butyramide (0.22 g, 69%).

Provenance & Evidence