Citric Acid → HCID 57302818, compound

HRID 1004511Notes

Reaction equation

HRID 1004511 reaction equation
C([O:3][C:4](=[O:43])[C@@H:5]([NH:33][S:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:36])=[O:35])[CH2:6][NH:7][C:8](=[O:32])[CH2:9][CH2:10][NH:11][C:12](=[O:31])[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:17][CH2:16]1)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:37]1([S:34]([NH:33][C@@H:5]([CH2:6][NH:7][C:8](=[O:32])[CH2:9][CH2:10][NH:11][C:12](=[O:31])[CH2:13][O:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:22])[CH2:17][CH2:16]2)[C:4]([OH:43])=[O:3])(=[O:36])=[O:35])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 70182006HCID 70182006, compound

Product 1

HCID 57302818HCID 57302818, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (144 mg) obtained in the above (2) is dissolved in DMF (3 ml), and thereto is added 1N aqueous sodium hydroxide solution (698 μl) under ice-cooling, and the mixture is stirred for 1.5 hour. The pH value thereof is adjusted to pH 2 with 10% aqueous citric acid solution, and extracted three times with ethyl acetate. The extract is washed twice with a saturated brine, and dried over anhydrous magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure to give the title compound (92 mg).

Workup

  1. temperaturecooling
  2. extractionextracted three times with ethyl acetate
  3. washThe extract is washed twice with a saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant is removed by filtration
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-592e67c0b2b1469fbf4496fe2216bebf
Source dataset
uspto-grants-2000_04
Patent number
US06048854

Reaction notes

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