Sodium Hydroxide → rac-(3R,4R)-1-((benzyloxy)carbonyl)-4-(trifluoromethyl)pyrrolidine-3-carboxylic acid

HRID 1378391노트

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HRID 1378391 반응식
C([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([F:14])([F:13])[F:12])[CH2:9][N:8]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH2:18]([O:17][C:15]([N:8]1[CH2:9][C@@H:10]([C:11]([F:12])([F:13])[F:14])[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 70207149HCID 70207149, 화합물

생성물 1

HCID 70207030rac-(3R,4R)-1-((benzyloxy)carbonyl)-4-(trifluoromethyl)pyrrolidine-3-carboxylic acid수율 95.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

In 92 ml of ethanol, is dissolved 15.8 g (45.8 mmol) of trans-1-benzyloxycarbonyl-4-trifluoromethylpyrrolidine-3-carboxylic acid ethyl ester. To the above solution, is added 46 ml of 2N sodium hydroxide on cooling with ice. The mixture is stirred at 0° C. for 1 hour and then concentrated under reduced pressure. The residue is dissolved in 100 ml of water. The solution is washed with diethyl ether. The water phase is adjusted to pH 3 with citric acid. The solution is extracted twice with dichloromethane. The organic phases were put together and dried over anhydrous magnesium sulfate. The dried organic phase was concentrated under reduced pressure to give 13.84 g of the objective substance as a colorless powder (yield 95.3%).

후처리

  1. temperatureon cooling with ice
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue is dissolved in 100 ml of water
  4. washThe solution is washed with diethyl ether
  5. extractionThe solution is extracted twice with dichloromethane
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe dried organic phase was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1666cf2ab13b4a7c8878f9347eab5387
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668147

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