Acetic Acid → HCID 68430972, compound

HRID 384134Notes

Reaction equation

HRID 384134 reaction equation
[C:1]([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]([NH2:28])[CH:23]=3)=[CH:15][CH:14]=2)[O:10][N:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:29]([BH3-])#N.[Na+].[C:33](O)(=O)[CH3:34]>CO.CC(C)=O.[Na+].C(=O)([O-])O>[C:1]([O:7][C:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][CH:33]([CH3:34])[CH3:29])[CH:23]=3)=[CH:17][CH:18]=2)[O:10][N:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 68430732HCID 68430732, compound

Product 1

HCID 68430972HCID 68430972, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-(4-(2-(3-aminophenyl)ethoxy)phenyl)-3-isoxazolyl pivalate (27.6 mg) in methanol (1 ml), 0.020 ml of acetone, 19.2 mg of sodium cyanoborohydride and 0.05 ml of acetic acid were added, and the reaction solution was stirred at room temperature for 2 hours. The reaction solution was diluted with saturated aqueous hydrogen carbonate sodium, 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., ethyl acetate/hexane (50:50)) to afford the title compound as a colorless oil.

Workup

  1. extractionextracted 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., ethyl acetate/hexane (50:50))

Sources & evidence

ORD record
ord-1db31efa18e9456480933e04a46e8489
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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