Methyl chloroformate → 3-Alanylamino-1,5-cyclohexadiene carboxylic acid hydrochloride

Participants

Reaction Steps

A solution of 188 mg (1 m mole) of tert-butoxycarbonylalanine in 5 ml of dichloromethane is treated with 101 mg (1 m mole) of triethylamine and 94 mg (1 m mole) of methyl chloroformate then added to a solution of 190 mg (1 m mole) of methyl 3-amino-1,5-cyclohexadienecarboxylate hydrochloride and 101 mg (1 m mole) of triethylamine in 5 ml of dichloromethane. After 1 hour at 25° C. the solution is washed with water, dried and evaporated. The residue is treated for 3 hours at 25° C. with 3 ml of methanol, 100 mg of sodium hydroxide and 2 ml of water then acidifie and extracted with dichloromethane. The organic phase is dryed and concentrated. The residue is treated with 7 ml of methanol containing 3.5 ml of 5% HCl for 18 hours at 25° C. then concentrated to afford 3-alanylamino-1,5 -cyclohexadiene carboxylic acid hydrochloride.

Provenance & Evidence