HCID 118276922, compound → HCID 118277087, compound

Participants

Reaction Conditions

Reaction Steps

In a second reaction of the same scale, under comparable conditions, and using comparable procedures, the initially isolated material consisted exclusively of the non-cyclized form (methyl 4-amino-3-(3-aminophenyl)-3-methyl-butanoate) MS (ESI+): m/z=223.20 (M+H)+. The crude material was dissolved/suspended in a sealed tube in toluene (about 25 mL) and heated to about 100° C. (oil bath temperature) for overnight to facilitate lactam formation (TLC reaction control). The organic solution was evaporated under reduced pressure using a rotary evaporator to afford a beige-brown waxy solid that was further purified by silica gel column chromatography using mixtures of dichloromethane (DCM) and methanol (MeOH) as eluent (DCM/MeOH=95:5→93:7) to afford the title compound (4c) as a beige solid. The analytical data corresponded to the proposed structure and was identical to that obtained from the direct lactamization method.

Provenance & Evidence