Reaction #3129

Reaction equation

(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

Yield 35.0%

Solvents

pyridine

ethyl acetate

pyridine

Conditions

Workup

1. 1
   ExtractionThe target substance was extracted from the mixture by ethyl acetate
2. 2
   WashThe extract was washed with saturated sodium chloride solution
3. 3
   Dryingwas dried over anhydrous sodium sulfate
4. 4
   ConcentrationThis solution was concentrated under reduced pressure
5. 5
   Otherwas 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)

Procedure

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