Sodium hydride → HCID 14306107, compound

Participants

Reaction Steps

In 5 ml of N,N-dimethylformamide solution was dissoved 838 mg of 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylic acid. To the solution was added 120 mg of sodium hydride (60% oil). To the mixture was added 648 mg of 4-nitrobenzyl bromide, followed by stirring at room temperature for 2.5 hours. To the reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, which was subjected to extraction with ethyl acetate. The aqueous layer was then dried (MgSO4), followed by removal of the solvent by evaporation. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 687 mg of 4-nitrobenzyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate as colorless crystals, m.p. 127-127.5° C.

Provenance & Evidence