Citric Acid → HCID 178437347, compound

HRID 384140Notes

Reaction equation

HRID 384140 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22]CC)=O)=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.C(O)(=O)CC([CH2:32][C:33](O)=O)(C(O)=O)O.[NH2:38][OH:39]>O1CCCC1.C(O)C.[OH-].[Na+]>[CH2:32]([C:19]1[C:20]([OH:22])=[N:38][O:39][C:18]=1[C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:17][CH:16]=1)[CH3:33]

Participants

7

Reactant 3

HCID 311Citric AcidHCID 787HydroxylamineHCID 68430535HCID 68430535, compound

Product 1

HCID 178437347HCID 178437347, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a mixed solution of ethyl 3-(4-(2-(3-methoxyphenyl)ethoxy)phenyl)propionate (75 mg) in tetrahydrofuran (1 ml) and ethanol (0.5 ml), 0.041 ml of hydroxylamine (50% aqueous solution) and 0.277 ml of 2.5N aqueous sodium hydroxide were added, and the reaction solution was stirred overnight at room temperature. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., ethyl acetate/hexane (25:75)) to afford the title compound as a white solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue obtained
  5. customwas purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., ethyl acetate/hexane (25:75))

Sources & evidence

ORD record
ord-eb5e834e393a4d1ea053b494d2dd3100
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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