Pyridine, hydrofluoride (1:1) → methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate

HRID 3028

Reaktionsgleichung

Reaktionsgleichung von HRID 3028
N1C=CC=CC=1.F.[CH3:8][O:9][C:10](=[O:54])[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:32][Si](C(C)(C)C)(C)C)[CH2:25][C@H:26]([CH3:31])[CH2:27][CH2:28][CH2:29][CH3:30])[C@H:20]([O:40][Si](C(C)(C)C)(C)C)[CH2:19][C:18]=1[O:48][C:49](=[O:53])[CH:50]([CH3:52])[CH3:51]>>[CH3:8][O:9][C:10](=[O:54])[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]([OH:32])[CH2:25][C@H:26]([CH3:31])[CH2:27][CH2:28][CH2:29][CH3:30])[C@H:20]([OH:40])[CH2:19][C:18]=1[O:48][C:49](=[O:53])[CH:50]([CH3:52])[CH3:51]

Komponenten

3

Edukt 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 22883798methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate

Produkt 1

HCID 22883799methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoateAusbeute 64 %

Versuchsvorschrift

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.6 ml) and methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (466 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (192 mg, 64%).

Quellen und Nachweise

ORD-Eintrag
ord-e25048cd0b1a4d4a97c39af9be62f679
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731452

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