Citric Acid → HCID 23111681, compound

HRID 1163318Notes

Reaction equation

HRID 1163318 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([N:12]([CH2:16][C:17]3[CH:39]=[CH:38][C:20]([CH2:21][O:22][C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[CH:28]([CH2:32][C:33]([O:35]CC)=[O:34])[CH2:27][CH2:26]5)=[CH:19][CH:18]=3)[CH2:13][CH2:14][CH3:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.O1CCCC1>[C:1]1([C:7]2[N:8]=[C:9]([N:12]([CH2:16][C:17]3[CH:39]=[CH:38][C:20]([CH2:21][O:22][C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[CH:28]([CH2:32][C:33]([OH:35])=[O:34])[CH2:27][CH2:26]5)=[CH:19][CH:18]=3)[CH2:13][CH2:14][CH3:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 58755267HCID 58755267, compound

Product 1

HCID 23111681HCID 23111681, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl {5-[(4-{[(4-phenyl-1,3-thiazol-2-yl)(propyl)amino]methyl}benzyl)oxy]-2,3-dihydro-1H-inden-1-yl}acetate (0.684 g, 1.17 mmol) in a mixed solvent of ethanol (6 mL) and tetrahydrofuran (6 mL) was added 2 M aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 24 hr. Water was added to the reaction mixture, and the mixture was neutralized with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30%-80% ethyl acetate/hexane) and recrystallized from ethyl acetate-hexane to give the title compound (0.393 g, yield 66%) as colorless prism crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (30%-80% ethyl acetate/hexane)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8fd1ae266cf1412ea06644bb53d1dcb1
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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