Sodium hydride → HCID 58303817, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 751 mg (1.85 mmol) of (+/−)-(2S,3S)-9-(benzyloxy)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one in 7 mL of DMF was added 81 mg (2.03 mmol) of sodium hydride (60% dispersion in mineral oil). The mixture was stirred at 22° C. for 30 minutes. In a separate flask, 408 mg (2.03 mmol) of 2-(dimethylamino)ethylchloride hydrochloride and 81 mg (2,03 mmol) of sodium hydride (60% dispersion in mineral oil), was added to 7 mL of DMF. The mixture was stirred for 30 minutes at 22° C. and then added to the former mixture. The reaction was heated to 45° C. and stirred for 27 hours. A mixture of 1:1 saturated NaHCO3 and water was added to the reaction, and the mixture was extracted with ethyl acetate (3×). The organic layers were combined, washed with brine, dried (Na2SO4), and evaporated. The resulting crude product was purified by flash chromatography on silica gel, eluting first with DCM then gradually increasing to 3.5% methanol/DCM to give (+/−)-(2S,3S)-9-(benzyloxy)-5-(2-(dimethylamino)ethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one.

Provenance & Evidence