Pyridine, hydrofluoride (1:1) → (11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienamide

HRID 3038

Reaction equation

HRID 3038 reaction equation
N1C=CC=CC=1.F.[C:8]([O:13][C:14]1[CH2:27][C@@H:26]([O:28][Si](C(C)(C)C)(C)C)[C@H:25](/[CH:36]=[CH:37]/[C@@H:38]([O:44][Si](C(C)(C)C)(C)C)[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:15]=1[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])(=[O:12])[CH2:9][CH2:10][CH3:11]>>[C:8]([O:13][C:14]1[CH2:27][C@@H:26]([OH:28])[C@H:25](/[CH:36]=[CH:37]/[C@@H:38]([OH:44])[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:15]=1[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])(=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

3

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 22883778(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide

Product 1

HCID 22883781(11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienamideYield 91%

Procedure

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide (169 mg), the same procedure was followed as in Example 2 to obtain (11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienamide (101 mg, 91%).

Sources & evidence

ORD record
ord-e7a5f5fa47d44c41aa8f5e9d244fb7f5
Source dataset
uspto-grants-1998_03
Patent number
US05731452

Linked notes

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