Diethyl Carbonate → HCID 19956142, compound

Participants

Reaction Steps

1.1 g of 3-(4-chloromethylphenyl)-5(R)-[4-(1,2di-benzyloxycarbonylethyl)piperazinomethyl]oxazolidin-2-one [obtainable by reaction of 4-chloromethylaniline with 2,3-epoxypropan-1-ol to give N-(4-chloro-methylphenyl)-2,3-dihydroxypropylamine, reaction with diethyl carbonate in the presence of K tert-butoxide to give 3-(4-chloromethylphenyl)-5-hydroxymethyl-oxazolidin-2-one, subsequent esterification with methanesulfonyl chloride and reaction with 1-(1,2-dibenzyloxycarbonylethyl)piperazine], dissolved in 30 ml of DMF, are treated at room temperature with 0.9 g of freshly prepared guanidine, dissolved in 10 ml of DMF, and the mixture is stirred for two hours. After removal of the solvent and customary working up, 3-(4-guanidinylmethylphenyl)-5(R)-[4-(1,2-dibenzyloxycarbonylethyl)piperazinomethyl]oxazolidin-2-one is obtained.

Provenance & Evidence