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

HRID 262705

반응식

HRID 262705 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e1f65a28e4d34f1a8430ef1d8861e9b4
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04154935

연결된 노트

불러오는 중…