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

HRID 1066203Notes

Reaction equation

HRID 1066203 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-54b1b03981844960b8eb54f3e238e2b9
Source dataset
uspto-grants-2001_06
Patent number
US06242476B1

Reaction notes

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