Citric Acid → HCID 9916797, compound

HRID 2297729Notes

Reaction equation

HRID 2297729 reaction equation
[C:1]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:16][C:17]([N:19]([CH:25]([CH2:34][C:35]([O:37]CC)=[O:36])[CH2:26][S:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=[CH:3][CH:2]=1.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:1]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:16][C:17]([N:19]([CH:25]([CH2:34][C:35]([OH:37])=[O:36])[CH2:26][S:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 9874043HCID 9874043, compound

Product 1

HCID 9916797HCID 9916797, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2S)-3-(4-Biphenylyl)-N-butyl-2-[3-[(1RS)-1-(ethoxycarbonylmethyl)-2-(phenylthio)ethyl]-3-isoamylureido]propionamide (Compound No. 38-1, 402 mg) is dissolved in ethanol(2 ml), a 1 N aqueous lithium hydroxide solution (0.96 ml) is added thereto, and the mixture is stirred at room temperature for 45minutes. A 10% aqueous citric acid solution is added to the reaction mixture, and the whole is extracted with ether. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 386 mg (quantitatively) of the titled compound (Compound No. 39-1) as noncrystalline powder.

Workup

  1. extractionthe whole is extracted with ether
  2. washThe organic layer is washed with water and saturated brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-628d05e1fb404847925d9f8a75307749
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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