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

HRID 3030

Reaction equation

N1C=CC=CC=1.F.[C:8]([O:13][C:14]1[CH2:31][C@@H:30]([O:32][Si](C(C)(C)C)(C)C)[C@H:29](/[CH:40]=[CH:41]/[C@@H:42]([O:50][Si](C(C)(C)C)(C)C)[CH2:43][C@H:44]([CH3:49])[CH2:45][CH2:46][CH2:47][CH3:48])[C:15]=1[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])(=[O:12])[CH2:9][CH2:10][CH3:11]>>[C:8]([O:13][C:14]1[CH2:31][C@@H:30]([OH:32])[C@H:29](/[CH:40]=[CH:41]/[C@@H:42]([OH:50])[CH2:43][C@H:44]([CH3:49])[CH2:45][CH2:46][CH2:47][CH3:48])[C:15]=1[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])(=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)

HCID 22883786butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate

Product 1

HCID 86752334butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoateYield 72%

Procedure

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (138 mg), the same procedure as in Example 2 was performed to obtain butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (69 mg, 72%).

Sources & evidence

ORD record: ord-947e00ce913b48258528de610493e045
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731452

Linked notes

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