Hydrochloric Acid → HCID 86738732, compound

Participants

Reaction Steps

To a mixture of 100 mg of (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15- dihydroxyprost-13-enoic acid (prepared as described in Example 2), 1.5 ml of N,N-dimethylformamide and 37 μl of triethylamine was added 35 μl of isobutyl chloroformate at 0° C., and the mixture was stirred at that temperature for 25 minutes. To it was added a mixture of 128 mg of sodium methanesulphonylamide and 0.233 ml of hexamethylphosphoramide at room temperature, and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was acidified to pH 4-5 with dilute hydrochloric acid, extracted with ethyl acetate, the extract washed with water, and a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a 5% v/v solution of methanol in ethyl acetate as eluent to give 75 mg of the title compound having the following physical characteristics.

Provenance & Evidence