Citric Acid → HCID 22350974, compound

HRID 896620Notes

Reaction equation

HRID 896620 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:15][CH2:16][CH2:17][N:18]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:21][S:20][C:19]1=[N:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[O:38][CH3:39])[CH2:9][C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:1]([O:5][C:6]([N:8]([CH2:15][CH2:16][CH2:17][N:18]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:21][S:20][C:19]1=[N:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[O:38][CH3:39])[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22350969HCID 22350969, compound

Product 1

HCID 22350974HCID 22350974, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (3 g) obtained in Example 321 (1) in ethanol (5 ml) was added dropwise a 4N aqueous sodium hydroxide solution (5 ml), and the mixture was stirred at room temperature for 4 hours. To the reaction mixture was added water, and the mixture was acidified with a 10% aqueous citric acid solution, and extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (2.92 g) as foam. (2) N-{3-[2-[(4-Chloro-2-methoxyphenyl)imino]-4-(4-fluorophenyl)thiazol-3 (2H)-yl]propyl}glycine

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ab40282dcf7842339999c3de69e6a659
Source dataset
uspto-grants-2005_07
Patent number
US06919361B2

Reaction notes

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