4-Methylmorpholine → HCID 131733463, compound

Participants

Reaction Steps

To a solution of N-(methoxycarbonyl)-β-phenyl-L-phenylalanine (3.2 g, 10.6 mmol) in dichloromethane (70 mL) was cooled to −15° C., and then was added N-methylmorpholine (1.17 mL, 10.6 mmol) and isobutyl chloroformate and the mixture was stirred for 30 minutes. A solution of prop-2-en-1-yl[(1R)-1-{5-[(1S)-1-amino-2,2,2-trifluoroethyl]thiophen-2-yl}-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]carbamate (3.1 g, 7.07 mmol) and Hunig's base (1.48 mL, 8.48 mmol) in dichloromethane (70 mL) cooled to −15° C. was added to the mixed anhydride solution. The mixture was allowed to warm up to room temperature by stirring overnight. Sodium bicarbonate was added and the phases were separated using a phase separator and concentrated under reduced pressure. The crude was purified on silica gel using 10% to 60% ethyl acetate in hexane to provide the title compound as an oil. MS: m/z=742.2 (MNa+).

Provenance & Evidence