Pyridine, hydrofluoride (1:1) → HCID 22883832, compound

HRID 3039Notes

Reaction equation

N1C=CC=CC=1.F.[CH2:8]([N:10]([CH2:54][CH3:55])[C:11](=[O:53])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17][C:18]1[C@@H:22](/[CH:23]=[CH:24]/[C@@H:25]([O:31][Si](C(C)(C)C)(C)C)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C@H:21]([O:39][Si](C(C)(C)C)(C)C)[CH2:20][C:19]=1[O:47][C:48](=[O:52])[CH2:49][CH2:50][CH3:51])[CH3:9]>>[CH2:54]([N:10]([CH2:8][CH3:9])[C:11](=[O:53])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17][C:18]1[C@@H:22](/[CH:23]=[CH:24]/[C@@H:25]([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C@H:21]([OH:39])[CH2:20][C:19]=1[O:47][C:48](=[O:52])[CH2:49][CH2:50][CH3:51])[CH3:55]

Participants

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)

HCID 22883830HCID 22883830, compound

Product 1

HCID 22883832HCID 22883832, compoundYield 87.2%

Procedure

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide (169 mg), the same procedure as in Example 2 was performed to obtain N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienamide (101 mg, 78%).

Sources & evidence

ORD record: ord-77b94b1df1cb49efa2184366a550397e
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731452

Reaction notes

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