Sodium Hydroxide → 2-Hydroxy-2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)acetic acid

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Reaction Steps

To a mixture of 2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylic acid, which can be represented as 2-(2-tert-pentyloxycarbonylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylic acid, (1.7 g.), sodium bicarbonate (0.5 g.), ethanol (10 ml.) and water (10 ml.) was added sodium borohydride (0.23 g.) under stirring and ice-cooling, and then the mixture was stirred for 1 hour at the same temperature. After the reaction, the reaction mixture was concentrated slightly. To the remaining reaction mixture were added 1 N sodium hydroxide aqueous solution (6 ml.) and diethyl ether (20 ml.), and then the aqueous layer was separated. To the aqueous layer was added ethyl acetate, and the mixture was adjusted to pH 1 to 2 with 10% hydrochloric acid and then the ethyl acetate layer was separated therefrom. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then treated with activated charcoal. The solvent was distilled off from the ethyl acetate layer to give brown powder of 2-hydroxy-2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)acetic acid, which can be represented as 2-hydroxy-2-(2-tert-pentyloxycarbonylimino-2,3-dihydro-1,3-thiazol-4-yl)acetic acid, (1.5 g.).

Provenance & Evidence