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

HRID 1456611ノート

反応式

HRID 1456611 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-06979b0ebfa8452fbd08a54a490553e8
出典データセット
uspto-grants-1998_12
特許番号
US05843992

反応ノート

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