Citric Acid → HCID 178456744, compound

HRID 384135Notes

Reaction equation

HRID 384135 reaction equation
C([O:7][C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][CH:29]([CH3:31])[CH3:30])[CH:23]=3)=[CH:15][CH:14]=2)[O:10][N:9]=1)(=O)C(C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.[OH-].[Na+]>[CH:29]([NH:28][C:24]1[CH:23]=[C:22]([CH2:21][CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([C:11]3[O:10][N:9]=[C:8]([OH:7])[CH:12]=3)=[CH:14][CH:15]=2)[CH:27]=[CH:26][CH:25]=1)([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 311Citric AcidHCID 68430972HCID 68430972, compound

Product 1

HCID 178456744HCID 178456744, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 5-(4-(2-(3-(isopropylamino)phenyl)ethoxy)phenyl)-3-isoxazolyl pivalate (24.9 mg) in methanol (1 ml), 0.05 ml of 4N aqueous sodium hydroxide was added, and the reaction solution was stirred at room temperature for 1 hour. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with chloroform and dried over anhydrous magnesium 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., chloroform/methanol (90:10)) to afford the title compound as a colorless amorphous matter.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialdried over anhydrous magnesium 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., chloroform/methanol (90:10))

Sources & evidence

ORD record
ord-35dc0b6ecb58479bb7ec7c2a80bcf8f7
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

Loading…