Triphenylphosphine → (13E)-(6RS,9alpha,11alpha,15S)-6,9-epithio-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid 1,3-bisstearoyloxy-2-propyl ester

Participants

Reaction Steps

Under an atmosphere of nitrogen, a mixture of 122 mg of (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid [prepared from (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15-dihydroxyprost-13-enoic acid (prepared as described in Example 2) by the tetrahydropyran-2-ylation procedure described in Reference Example 1], 143 mg of 1,3-bisstearoyloxy-2-propanol, prepared as described above, 75 mg of dipyridyl disulphide, 90 mg of triphenylphosphine and 3 ml of xylene was stirred at room temperature for 2 hours, then at 40° C. for 2 hours, and at 80° C. overnight. The reaction mixture was poured into water, extracted with ethyl acetate, the extract was washed with water, and a threaded 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 mixture of cyclohexane and ethyl acetate (8:1) as eluent to give 51 mg of (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid 1,3-bisstearoyloxy-2-propyl ester having the following physical characteristic:

Provenance & Evidence