Sodium Chloride → HCID 46244897, compound

Participants

Reaction Conditions

Reaction Steps

(+/−)-2-(Benzoyloxymethyl)-1,3-oxathiolane (0.71 mmol, 160 mg) was dissolved in acetonitrile (0.6 mL) in a 25-mL round-bottomed flask. A 0.1 M phosphoric acid-phosphate buffer solution (15 mL) adjusted to pH 7.0 was added to the reaction followed by 21 units of cholesterol esterase from bovine pancreas (Sigma #C3766). The reaction was stirred at approximately 4° C. for a period of up to 24 h while maintaining the pH of the reaction media at pH 7.0 with 1 M sodium hydroxide solution. The progress of the reaction may be monitored by gas chromatography for disappearance of the (+/)-2-(benzoyloxymethyl)-1,3-oxathiolane and/or by chiral HPLC for enantiomeric enrichment. When the reaction had proceeded to about 50% conversion, the mixture was saturated with sodium chloride and extracted with methyl tert-butyl ether (5×5 mL). Concentration of the extracts afforded a crude product that was purified by silica gel chromatography to give 2(R)-(benzoyloxymethyl)-1,3-oxathiolane (68 mg) and 2(S)-(hydroxymethyl)-1,3-oxathiolane (38 mg).

Provenance & Evidence