Benzyl chloroformate → 1-[(Benzyloxy)carbonyl]-3-hydroxyazetidine-3-carboxylic acid

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Reaction Steps

To a solution of 2.5 g (16.3 mmoles) of 3-hydroxyazetidine-3-carboxylic acid (prepared in Example 6) dissolved in a solution of 2.04 g of sodium hydroxide in 54 ml of water is added 3.34 g (1.2 equivalents) of benzyloxycarbonyl chloride under stirring at room temperature, and the mixture is stirred overnight and then mixed with 10% aqueous sodium hydroxide solution. The resulting alkali solution is washed with ether, adjusted to pH 1 with 10% hydrochloric acid and extracted with ether. The extract is washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue is crystallized from n-pentane and then recrystallized from ether-n-pentane to yield 3.137 g of 1-benzyloxycarbonyl-3-hydroxyazetidine-3-carboxylic acid as needles, mp. 134°-136° C., in 76% yield.

Provenance & Evidence