Water → Methyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate

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Reaction Steps

In 100 ml of N,N-dimethylformamide was dissolved 27.93 g of 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylic acid obtained by the method described in Journal of Organic Chemistry, 6 878 (1941). To the solution was added 4.0 g of sodium hydride (60% oil), to which was further added 28.4 of methyl iodide, and the reaction was allowed to proceed at room temperature for 4 hours. The reaction mixture was supplemented with 14.2 g of methyl iodide, which was stirred for further 3 hours. The reaction solution was poured into water, which was subjected to extraction with ethyl acetate. The organic layer was washed with sodium hydrogen carbonate and a saturated saline solution, successively, followed by drying (MgSO4). The solvent was evaporated off, and the crystals which separated out were collected by filtration, followed by washing with ether to give 27.25 g of methyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate as colorless crystals, m.p. 134-134.5° C.

Provenance & Evidence