Methyl chloroformate → HCID 86587225, compound

Participants

Reaction Steps

To a stirred solution of N-[(3R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-amino-β-alanine (250 mg) in a mixture of tetrahydrofuran (5 mL) and 1 N-aqueous sodium hydroxide solution (1.16 mL) was added dropwise methyl chloroformate (45 μL) at 4° C. After 15 minutes, the reaction mixture was acidified with 5% aqueous potassium hydrogensulfate solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The organic layer was evaporated and the residue was treated with 4 N-hydrogen chloride in ethyl acetate. The resulting insoluble material was collected by filtration and dried. The dry material was dissolved in water. Thus obtained solution was neutralized with an aqueous saturated sodium hydrogencarbonate solution and lyophilized. The residue was purified by ODS column chromatography (Daisogel-120sp®) eluting with 2, 5 and 8% CH3CN/H2O and lyophilized to give N-[(3R)-1-{3-(4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-methoxycarbonylamino-β-alanine (162 mg, 71.4%) as an amorphous powder.

Provenance & Evidence