Dicyclohexylcarbodiimide → N,S-Diacetyl-DL-cysteinyl-L-proline tert-butyl ester

HRID 1762515노트

반응식

HRID 1762515 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].OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:38]([NH:41][CH:42]([C:48](O)=[O:49])[CH2:43][S:44][C:45](=[O:47])[CH3:46])(=[O:40])[CH3:39]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:48](=[O:49])[CH:42]([CH2:43][S:44][C:45](=[O:47])[CH3:46])[NH:41][C:38](=[O:40])[CH3:39])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 4321391HCID 4321391, 화합물HCID 6453108L-Proline 1,1-dimethylethyl esterHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 14181603N,S-Diacetyl-DL-cysteinyl-L-proline tert-butyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of L-proline tert-butyl ester (0.85 g.) and hydroxybenzotriazole (0.67 g.) in methylene chloride (10 ml.) chilled in an ice bath, dicyclohexylcarbodiimide (1.03 g.) and N,S-diacetyl-D,L-cysteine (1.7 g.) are added in that order. After fifteen minutes, the ice bath is removed and the mixure is stirred at room temperature overnight. The precipitate is filtered off and the filtrate is washed with 10% potassium bisulfate, water, saturated sodium bicarbonate, and water. The organic phase is dried and concentrated to dryness in vacuo to give N,S-diacetyl-D,L-cysteinyl-L-proline tert-butyl ester as an oil. Rf =0.25 (silica gel, ethylacetate).

후처리

  1. waitAfter fifteen minutes
  2. customthe ice bath is removed
  3. filtrationThe precipitate is filtered off
  4. washthe filtrate is washed with 10% potassium bisulfate, water, saturated sodium bicarbonate, and water
  5. customThe organic phase is dried
  6. concentrationconcentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-ad166a250b0d42568fe8f888c9cacc5c
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04833152

반응 노트

불러오는 중…