Triethylamine → (13E)-(6RS,9alpha,11alpha,15S)-6,9-Epithio-11,15-dihydroxyprost-13-enoic acid 4-semicarbazonotolyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 98 mg of (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15-dihydroxyprost-13-enoic acid (prepared as described in Example 2) and 52 μl of triethylamine in 3 ml of acetone was added 49 μl of isobutyl chloroformate at 0° C., and the mixture was stirred at 0° C. for 30 minutes. To it were added 1.4 ml of pyridine and 202 mg of 4-hydroxybenzaldehyde semicarbazone at ambient temperature, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by recrystallization from acetonitrile to give 29.5 mg of the title compound having the following physical characteristics: melting point: 90°-91° C.;

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