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

HRID 3033

Reaktionsgleichung

Reaktionsgleichung von HRID 3033
N1C=CC=CC=1.F.C(#N)C.[C:11]([O:16][C:17]1[CH2:30][C@@H:29]([O:31][Si](C(C)(C)C)(C)C)[C@H:28](/[CH:39]=[CH:40]/[C@@H:41]([O:47][Si](C(C)(C)C)(C)C)[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:18]=1[S:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](O)=O)(=[O:15])[CH2:12][CH2:13][CH3:14].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.N1C=CC=CC=1>[C:11]([O:16][C:17]1[CH2:30][C@@H:29]([OH:31])[C@H:28](/[CH:39]=[CH:40]/[C@@H:41]([OH:47])[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:18]=1[S:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:15])[CH2:12][CH2:13][CH3:14]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 22883780(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid

Produkt 1

HCID 86752335(11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dieneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  1. extractionThe target substance was extracted from the mixture by ethyl acetate
  2. washThe extract was washed with saturated sodium chloride solution
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationThis solution was concentrated under reduced pressure
  5. customwas 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)

Quellen und Nachweise

ORD-Eintrag
ord-76f66933b8914bb1a7437f5254a0de57
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731452

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