Acetyl chloride → (3aR*,10aS*)-9-(4-Acetamidobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e]-[1,4]diazepin-10(1H)-one

Participants

Reaction Steps

To a suspension of (3aR*,10aS*)-9-(4-aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (198 mg, 0.4 mmol) in dichloromethane (1 mL) was added acetyl chloride (43 μL, 0.6 mmol) and the mixture was stirred at room temperature for 20 minutes. This reaction mixture was diluted with dichloromethane (3 mL) and, after saturated aqueous NaHCO3 solution (2 mL) was added, the mixture was further stirred. The aqueous layer was then separated and the organic layer was washed with water, dried over MgSO4, and concentrated under reduced pressure. The residue was crystallized from dichloromethane-ethanol and recrystallized from chloroform-ethanol to provide 72 mg (yield 34%) of the title compound. m.p. 303°-306° C.

Provenance & Evidence