Pyridine, hydrofluoride (1:1) → methyl(11R,13E,15S)-9-benzoyloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienoate

HRID 3032

Reaktionsgleichung

Reaktionsgleichung von HRID 3032
N1C=CC=CC=1.F.[CH3:8][O:9][C:10](=[O:55])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]1[C@@H:21](/[CH:22]=[CH:23]/[C@@H:24]([O:30][Si](C(C)(C)C)(C)C)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:20]([O:38][Si](C(C)(C)C)(C)C)[CH2:19][C:18]=1[O:46][C:47](=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>>[C:47]([O:46][C:18]1[CH2:19][C@@H:20]([OH:38])[C@H:21](/[CH:22]=[CH:23]/[C@@H:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:17]=1[S:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([O:9][CH3:8])=[O:55])(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Komponenten

3

Edukt 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 22883804methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate

Produkt 1

HCID 22883805methyl(11R,13E,15S)-9-benzoyloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienoateAusbeute 88,3 %

Versuchsvorschrift

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.3 ml) and methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (239 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,13E,15S)-9-benzoyloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienoate (144 mg, 86%).

Quellen und Nachweise

ORD-Eintrag
ord-a8c4e36b9c5748c2bdb42724db547b96
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731452

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