Formic Acid → HCID 131727858, compound

Participants

Reaction Steps

A solution of 3.13 g (3.96 mmol) of benzyl[1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)(2-fluoroethyl)carbamoyl]ethylcarbamoyl}-2-(2,4-dichlorobenzenesulfonylamino)ethyl]carbamate in 20 ml of formic acid was heated to 60° C. and stirred for 6 hours. The reaction mixture was concentrated in vacuo, diluted with EtOAc and washed with 1N NaHCO3 solution and brine. The organic phase was isolated, dried (MgSO4) and concentrated in vacuo. This crude substance was subjected to a flash chromatography on 120 g of SiO2 (elution with EtOAc/heptane, gradient 50-100%). 350 mg of the substance benzyl[6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-(2-fluoroethyl)-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate were obtained. Further elution of the column provided 980 mg of the compound corresponding to the benzyl[6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-(2-hydroxyethyl)-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate byproduct. The monoisotopic MW expected in the LC/MS=694 and the measured value of (M+H)=695 agree with the structure.

Provenance & Evidence