Acetonitrile → (11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-diene

HRID 3033

반응식

HRID 3033 반응식
N1C=CC=CC=1.F.C(#N)C.[C:11]([O:16][C:17]1[CH2:30][C@@H:29]([O:31][Si](C(C)(C)C)(C)C)[C@H:28](/[CH:39]=[CH:40]/[C@@H:41]([O:47][Si](C(C)(C)C)(C)C)[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:18]=1[S:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](O)=O)(=[O:15])[CH2:12][CH2:13][CH3:14].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.N1C=CC=CC=1>[C:11]([O:16][C:17]1[CH2:30][C@@H:29]([OH:31])[C@H:28](/[CH:39]=[CH:40]/[C@@H:41]([OH:47])[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:18]=1[S:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:15])[CH2:12][CH2:13][CH3:14]

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 22883780(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid

생성물 1

HCID 86752335(11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-diene수율 35%

시약·촉매·용매 2

HCID 1049Pyridine용매2회HCID 8857Ethyl Acetate용매

실험 절차

A hydrogen fluoride-pyridine solution (0.1 ml) was added to a solution of ice-cooled acetonitrile (1 ml) and pyridine (0.1 ml), then a pyridine (0.1 ml) solution of (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid (79 mg) was added. The ice bath was detached, then the solution was stirred for 20 hours while raising it to room temperature. The reaction solution was poured into a mixture of ethyl acetate and saturated sodium hydrogencarbonate. The target substance was extracted from the mixture by ethyl acetate. The extract was washed with saturated sodium chloride solution, then was dried over anhydrous sodium sulfate. This solution was concentrated under reduced pressure, then was purified by a preparative TLC (Merck TLC plate silica gel 60 F254, 20×20 cm, layer thickness 0.25 mm, 2 pieces, ethyl acetate:hexane 4:1) to obtain (11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-diene acid (17 mg, 33%).

후처리

  1. extractionThe target substance was extracted from the mixture by ethyl acetate
  2. washThe extract was washed with saturated sodium chloride solution
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationThis solution was concentrated under reduced pressure
  5. customwas purified by a preparative TLC (Merck TLC plate silica gel 60 F254, 20×20 cm, layer thickness 0.25 mm, 2 pieces, ethyl acetate:hexane 4:1)

출처 및 근거

ORD 기록
ord-76f66933b8914bb1a7437f5254a0de57
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731452

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