Réaction #3129

Équation de réaction

(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid

sodium hydrogencarbonate

hydrogen fluoride-pyridine

acetonitrile

→

(11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-diene

Rendement 35.0%

Solvants

pyridine

ethyl acetate

pyridine

Conditions de réaction

Traitement

1. 1
   ExtractionThe target substance was extracted from the mixture by ethyl acetate
2. 2
   LavageThe extract was washed with saturated sodium chloride solution
3. 3
   Séchagewas dried over anhydrous sodium sulfate
4. 4
   ConcentrationThis solution was concentrated under reduced pressure
5. 5
   Autrewas purified by a preparative TLC (Merck TLC plate silica gel 60 F254, 20×20 cm, layer thickness 0.25 mm, 2 pieces, ethyl acetate:hexane 4:1)

Mode opératoire

A hydrogen fluoride-pyridine solution (0.1 ml) was added to a solution of ice-cooled acetonitrile (1 ml) and pyridine (0.1 ml), then a pyridine (0.1 ml) solution of (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid (79 mg) was added. The ice bath was detached, then the solution was stirred for 20 hours while raising it to room temperature. The reaction solution was poured into a mixture of ethyl acetate and saturated sodium hydrogencarbonate. The target substance was extracted from the mixture by ethyl acetate. The extract was washed with saturated sodium chloride solution, then was dried over anhydrous sodium sulfate. This solution was concentrated under reduced pressure, then was purified by a preparative TLC (Merck TLC plate silica gel 60 F254, 20×20 cm, layer thickness 0.25 mm, 2 pieces, ethyl acetate:hexane 4:1) to obtain (11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-diene acid (17 mg, 33%).

Source