Dimethylformamide → HCID 66971957, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottom flask was fitted with a condenser, stirbar and septa. 3(R)-Amino-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one D-pyroglutamic acid salt (10.0 g, 32.8 mmol), N,N-dimethylformamide (200 mL) and triethylamine (12 mL, 86.1 mmol) were added, giving a mixture which was heated to 120° C. To the resulting solution was added trityl chloride (9.04 g, 32.4 mmol). The reaction was then cooled to 60° C., maintained at 60° C. for 4 hours, and then allowed to slowly cool to room temperature. After 18 hours, the reaction mixture was diluted with diethyl ether (300 mL) and washed first with 400 mL 1:1 H2O:saturated aqueous NaCl solution, then with 2×100 mL H2O. The aqueous washes were combined and extracted with diethyl ether (100 mL). The organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo to give an oil which that purified via flash chromatography on silica gel (25% ethyl acetate/hexanes) to give the desired product.

Provenance & Evidence