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

HRID 3029

반응식

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: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:54])[C:50]([CH3:53])([CH3:52])[CH3:51]>>[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]([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:54])[C:50]([CH3:53])([CH3:52])[CH3:51]

참가 물질

반응물 2

HCID 64774Pyridine, hydrofluoride (1:1)

HCID 22883800methyl(11R,12S,13E,15S,17R)-9-pivaloyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate

생성물 1

HCID 22883801methyl(11R,13E,15S,17R)-9-pivaloyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate수율 55%

실험 절차

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.7 ml) and methyl(11R,12S,13E,15S,17R)-9-pivaloyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (564 mg), the same procedure was performed as in Example 2 was performed to obtain methyl(11R,13E,15S,17R)-9-pivaloyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (211 mg, 55%).

출처 및 근거

ORD 기록: ord-4530e01b498e4c59a4e74ef8002e38f6
출처 데이터셋: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05731452

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