Dicyclohexylcarbodiimide → N-(3-acetylthio-2-trifluoromethylpropanoyl)-L-proline tertbutyl ester

HRID 262705

反応式

HRID 262705 の反応式
[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:28]([S:31][CH2:32][CH:33]([C:37]([F:40])([F:39])[F:38])[C:34](O)=[O:35])(=[O:30])[CH3:29]>ClCCl>[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:34](=[O:35])[CH:33]([C:37]([F:38])([F:39])[F:40])[CH2:32][S:31][C:28](=[O:30])[CH3:29])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 128330143-Acetylthio-2-trifluoromethylpropanoic acid

生成物 1

HCID 54253056N-(3-acetylthio-2-trifluoromethylpropanoyl)-L-proline tertbutyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

L-proline tert-butyl ester (5.1 g.) is dissolved in dichloromethane (40 mg.) and the solution is stirred and chilled in an ice bath. Dicyclohexylcarbodiimide (6.2 g.) dissolved in dichloromethane (15 ml.) is added followed immediately by a solution of 3-acetylthio-2-trifluoromethylpropanoic acid (6.5 g.) in dichloromethane (5 ml.). After fifteen minutes stirring in the ice bath and sixteen hours at room temperature, the precipitate formed is filtered off and the filtrate is concentrated to dryness in vacuo. The residue is dissolved in ethyl acetate and washed neutral. The organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo to give 1-(3-acetylthio-2-trifluoromethylpropanoyl)-L-proline tert-butyl ester.

後処理

  1. temperaturechilled in an ice bath
  2. additionis added
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. concentrationthe filtrate is concentrated to dryness in vacuo
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washwashed neutral
  8. dry with materialThe organic phase is dried over magnesium sulfate
  9. concentrationconcentrated to dryness in vacuo

出典と根拠

ORDレコード
ord-e1f65a28e4d34f1a8430ef1d8861e9b4
出典データセット
uspto-grants-1979_05
特許番号
US04154935

関連ノート

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