Citric Acid → 1-[(2S)-3-Benzoylthio-2-methylpropionyl]-(4S)-4-(4-cyclohexylbenzylthio)-L-proline

HRID 1066203노트

반응식

HRID 1066203 반응식
CN(C)C=O.[CH2:6]([C:12]1[CH:27]=[CH:26][C:15]([CH2:16][S:17][C@@H:18]2[CH2:22][NH:21][C@H:20]([C:23]([OH:25])=[O:24])[CH2:19]2)=[CH:14][CH:13]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:28]([S:36][CH2:37][C@@H:38]([CH3:51])[C:39](OC1C=CC([N+]([O-])=O)=CC=1)=[O:40])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(N(CC)CC)C>[C:28]([S:36][CH2:37][C@@H:38]([CH3:51])[C:39]([N:21]1[CH2:22][C@@H:18]([S:17][CH2:16][C:15]2[CH:26]=[CH:27][C:12]([CH:6]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]3)=[CH:13][CH:14]=2)[CH2:19][C@H:20]1[C:23]([OH:25])=[O:24])=[O:40])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 6228DimethylformamideHCID 154536594-Nitrophenyl (2S)-3-benzoylthio-2-methylpropionateHCID 69535149(4S)-4-(4-hexylbenzylthio)-L-proline

생성물 1

HCID 206600501-[(2S)-3-Benzoylthio-2-methylpropionyl]-(4S)-4-(4-cyclohexylbenzylthio)-L-proline수율 81%

시약·촉매·용매 1

HCID 8471Triethylamine용매

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온도
0 °C

실험 절차

Dimethylformamide (4.5 ml) is added to (4S)-4-(4-hexylbenzylthio)-L-proline (430 mg), and the mixture is cooled to 0° C. To the mixture are added successively triethylamine (0.21 ml) and 4-nitrophenyl (2S)-3-(benzoylthio)-2-methylpropionate, and the obtained mixture is stirred at room temperature overnight. To the reaction mixture is added 10% citric acid, and the whole is extracted with ethyl acetate. The organic layer is washed with water and a saturated sodium chloride aqueous solution successively and dried over sodium sulfate. The residue obtained by concentration under reduced pressure is purified by silica gel column chromatography to give 580 mg (81%) of the titled compound as an amorphous substance.

후처리

  1. extractionthe whole is extracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. dry with materiala saturated sodium chloride aqueous solution successively and dried over sodium sulfate
  4. customThe residue obtained by concentration under reduced pressure
  5. customis purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-54b1b03981844960b8eb54f3e238e2b9
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06242476B1

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