Citric Acid → HCID 11295855, compound

HRID 732231Notes

Reaction equation

HRID 732231 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([S:20]([C:23]3[S:24][CH:25]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:27]=3)(=[O:22])=[O:21])[CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:34][CH2:35][C:36]([O:38]CC)=[O:37].[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH:16]([S:20]([C:23]3[S:24][CH:25]=[C:26]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:27]=3)(=[O:22])=[O:21])[CH2:17][CH2:18][CH3:19])=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:34][CH2:35][C:36]([OH:38])=[O:37]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23143253HCID 23143253, compound

Product 1

HCID 11295855HCID 11295855, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 3-{2-fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)sulfonyl]butyl}benzyl)oxy]phenyl}propanoate (0.360 g, 0.619 mmol) in a mixture of ethanol (1.5 mL) and tetrahydrofuran (3 mL) was added 1N aqueous sodium hydroxide solution (0.75 mL), and the mixture was stirred at 50° C. for 1.5 hr. Water was added to the reaction mixture, and the mixture was weak acidified 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 (ethyl acetate:hexane=30:70-80:20) and recrystallized from ethyl acetate-hexane to give the title compound (0.300 g, yield 88%) as colorless 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 (ethyl acetate:hexane=30:70-80:20)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3536623ffd154d6b8a7241f563494cb9
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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