Dicyclohexylcarbodiimide → 1-(3-Acetylthio-2-methylpropanoyl)-L-Proline tert-butyl Ester

HRID 262553노트

반응식

HRID 262553 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]([CH3:37])[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]([CH3:37])[CH2:32][S:31][C:28](=[O:30])[CH3:29])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 1180733-(Acetylthio)-2-methylpropanoic acidHCID 6453108L-Proline 1,1-dimethylethyl ester

생성물 1

HCID 141815171-(3-Acetylthio-2-methylpropanoyl)-L-Proline tert-butyl Ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

L-Proline tert-butyl ester (5.1 g.) is dissolved in dichloromethane (40 ml.) and the solution 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-methylpropanoic acid (4.9 g.) in dichloromethane (5 ml.). After 15 minutes stirring in the ice bath and 16 hours at room temperature, the precipitate 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. The residue 1-(3-acetylthio-2-methylpropanoyl)-L-proline tert-butyl ester is purified by column chromatography (silica gel-chloroform), yield 7.9 g.

후처리

  1. temperaturechilled in an ice bath
  2. additionis added
  3. filtrationthe precipitate is filtered off
  4. concentrationthe filtrate is concentrated to dryness in vacuo
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed neutral
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated to dryness in vacuo
  9. customThe residue 1-(3-acetylthio-2-methylpropanoyl)-L-proline tert-butyl ester is purified by column chromatography (silica gel-chloroform), yield 7.9 g

출처 및 근거

ORD 기록
ord-db34a6e8842b4727b6f92b97aa4be28c
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04154840

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