Sodium Hydroxide → (2S,3S)-3-Diphenylmethylcarbamoyloxirane-2-carboxylic acid

HRID 1456611노트

반응식

HRID 1456611 반응식
[C:1]1([CH:7]([NH:14][C:15]([C@H:17]2[O:19][C@@H:18]2[C:20]([O:22]CC)=[O:21])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:8]1([CH:7]([NH:14][C:15]([C@H:17]2[O:19][C@@H:18]2[C:20]([OH:22])=[O:21])=[O:16])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 57291692Ethyl (2S,3S)-3-diphenylmethylcarbamoyloxirane-2-carboxylate

생성물 1

HCID 9883544(2S,3S)-3-Diphenylmethylcarbamoyloxirane-2-carboxylic acid

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

In ethanol (300 mL) was dissolved ethyl (2S,3S)-3-diphenylmethylcarbamoyloxirane-2-carboxylate (5.50 g, 16.9 mmol.) obtained in Example 1. To the resulting solution was added a solution of 0.5N sodium hydroxide in ethanol (40.4 mL, 20.2 mmol.), and the mixture was stirred for 3 hours at room temperature. The solvent was distilled off under reduced pressure, and washed with two 100 mL portions of ethyl ether after addition of water (300 mL). The aqueous portion was made to show pH 1-2 by addition of 2N hydrochloric acid, and extracted with three 100 mL portions of ethyl acetate. The organic portion was washed with an aqueous sodium chloride saturated solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give the desired compound as a white crystalline powdery product (4.76 g, yield: 95%).

후처리

  1. customobtained in Example 1
  2. distillationThe solvent was distilled off under reduced pressure
  3. washwashed with two 100 mL portions of ethyl ether
  4. additionafter addition of water (300 mL)
  5. additionby addition of 2N hydrochloric acid
  6. extractionextracted with three 100 mL portions of ethyl acetate
  7. washThe organic portion was washed with an aqueous sodium chloride saturated solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-06979b0ebfa8452fbd08a54a490553e8
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843992

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