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

HRID 3037

反応式

HRID 3037 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-3a3271a594c4451684be2191aa815526
出典データセット
uspto-grants-1998_03
特許番号
US05731452

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