Triethylamine → (3aR*,10aS*)-4-(Phthalimidoacetyl)-9-(4-propionamidobenzyl)-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][l,4]diazepin-10(1H)-one (148 mg, 0.3 mmol) and triethylamine (50 μL, 0.36 mmol) in dichloromethane (3 mL) was added propionyl chloride (28 μL, 0.33 mmol) and the mixture was stirred at room temperature for 10 minutes. This reaction mixture was diluted with water and stirred. The aqueous layer was separated and the organic layer was dried over NaSO4 and concentrated under reduced pressure. The residue was crystallized from dichloromethane-ethanol-diethyl ether to provide 131 mg (yield 79%) of the title compound. m.p. 286.0°-286.5° C.

Provenance & Evidence