Citric Acid → HCID 20725181, compound

HRID 2297718Notes

Reaction equation

HRID 2297718 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:5](=[O:17])[NH:6][C@@H:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:8]([O:10]CC)=[O:9].[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(O)C>[OH:1][CH2:2][CH2:3][N:4]([CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:5](=[O:17])[NH:6][C@@H:7]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 86586957HCID 86586957, compound

Product 1

HCID 20725181HCID 20725181, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (2S)-2-[3-(2-hydroxyethyl)-3-phenethylureido]-4-methylvalerate (Compound No. 1-31, 1.00 g) is dissolved in a mixed solvent of tetrahydrofuran (3.5 ml)-ethanol (2.8 ml). A 2 N aqueous lithium hydroxide solution (1.7 ml) is added thereto under ice cooling, and the mixture is stirred under ice cooling for 25 minutes and further at room temperature for one hour. A 5% aqueous citric acid solution is added to the reaction mixture, and the whole is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.02 g (quantitatively) of the titled compound (Compound No. 15-1).

Workup

  1. extractionthe whole is extracted with ethyl acetate
  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

Sources & evidence

ORD record
ord-0ade1a40e5da4407974deb932655bf0e
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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