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

HRID 3037

反应方程式

HRID 3037 反应方程式
[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]

参与物

8

反应物 4

HCID 313海萝胶HCID 14923氨水HCID 62365氯甲酸异丁酯HCID 22883780(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid

产物 1

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

试剂、催化剂与溶剂 3

HCID 6344二氯甲烷溶剂HCID 8471三乙胺溶剂HCID 8857乙酸乙酯溶剂

实验过程

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%).

后处理

  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)

来源与证据

ORD记录
ord-3a3271a594c4451684be2191aa815526
来源数据集
uspto-grants-1998_03
专利号
US05731452

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