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

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Reaction Steps

In 100 ml of dimethylformamide was dissolved 27.93 g of 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylic acid prepared 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 then added 28.4 g of methyl iodide, followed by allowing the reaction to proceed at room temperature for 4 hours. To the resultant was added 28.4 g of methyl iodide, and the mixture was stirred for further 3 hours. The reaction mixture was added to water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, successively, then dried (MgSO4). The solvent was distilled off, and precipitating crystals 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