Hydrochloric Acid → HCID 18659459, compound

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Reaction Steps

A solution of 1.0g (2.19mmol) of (RS)-α-[[[(R)-2-(1-tert-butoxyformamido)-2-(methoxycarbonyl)-1,1-dimethylethyl]sulfonyl]methyl]hydrocinnamic acid was added dropwise at room temperature to 10 ml of 1.4 M hydrogen chloride in dioxan and stirred for a further 12 hours. After evaporation of the solvent under reduced pressure there was obtained a colourless foam which, without further purification and characterization, was dissolved in 8.5 ml of 1N sodium hydrogen carbonate solution and treated with 0.44 ml (3.07 mmol) of benzyl chloroformate. The thus-obtained suspension was stirred at room temperature for 12 hours. Subsequently, it was extracted twice with 250 ml of ether each time, the combined ether extracts were dried over magnesium sulphate and evaporated under reduced pressure. For purification, the oily crude product (1.05 g) was chromatographed on 50 g of silica gel firstly with methylene chloride then with a 95:5 mixture of methylene chloride and methanol as the eluent. There were obtained 430 mg of (RS)-α-[[[(R)- 2-(1-benzyloxyformamido)-2-(methoxycarbonyl)-1,1-dimethylethyl]sulfonyl]methyl]hydrocinnamic acid as a colourless foam, MS: 493 (M+H)+.

Provenance & Evidence