Hydrochloric Acid → (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide

HRID 3037

반응식

HRID 3037 반응식
[C:1]([O:6][C:7]1[CH2:20][C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C@H:18](/[CH:29]=[CH:30]/[C@@H:31]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:8]=1[S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16])(=[O:5])[CH2:2][CH2:3][CH3:4].ClC(OCC(C)C)=O.[OH-].[NH4+:54].Cl>C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)Cl>[C:1]([O:6][C:7]1[CH2:20][C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C@H:18](/[CH:29]=[CH:30]/[C@@H:31]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:8]=1[S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH2:54])=[O:16])(=[O:5])[CH2:2][CH2:3][CH3:4]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 22883780(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid

생성물 1

HCID 22883778(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide수율 84%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

A methylene chloride (3 ml) solution of (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid (201 mg) was cooled to -40° C., then isobutyl chloroformate (47 μl) and triethylamine (63 μl) were added to the solution which was then stirred as is at -40° C. for 30 minutes. Further 1 ml of 30% ammonium hydroxide solution was added and the mixture was stirred overnight while raising the temperature to room temperature. The reaction solution was diluted by ethyl acetate then was neutralized by dilute hydrochloric acid. The desired substance was extracted from the mixture by ethyl acetate and extract was successively washed by saturated sodium hydrogen carbonate and saturated sodium chloride solution. This solution was concentrated under reduced pressure, then was purified by silica gel column chromatography (45% ethyl acetate/hexane) to obtain (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide (169 mg, 84%).

후처리

  1. stirringthe mixture was stirred overnight
  2. extractionThe desired substance was extracted from the mixture by ethyl acetate
  3. extractionextract
  4. washwas successively washed by saturated sodium hydrogen carbonate and saturated sodium chloride solution
  5. concentrationThis solution was concentrated under reduced pressure
  6. customwas purified by silica gel column chromatography (45% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-3a3271a594c4451684be2191aa815526
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731452

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