Sodium Hydroxide → HCID 24951393, compound

HRID 1967578Notes

Reaction equation

HRID 1967578 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][N:6]([C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH:27]([CH2:29][CH3:30])[CH3:28])[CH:21]=2)=[C:14]([Cl:31])[CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])C.[OH-].[Na+]>CO.O>[CH:27]([C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[OH:26])[O:19][C:15]1[C:14]([Cl:31])=[CH:13][C:12]([N:6]([CH2:5][C:4]([OH:32])=[O:3])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:17][C:16]=1[Cl:18])([CH2:29][CH3:30])[CH3:28]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68556857HCID 68556857, compound

Product 1

HCID 24951393HCID 24951393, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The ester (0.77 g, 1.5 mmol) was dissolved in MeOH (18 mL) and to it a solution of NaOH (0.19 g, 4.75 mmol) in H2O (5.6 mL) was added and it was stirred at 60° C. for 1 hr. Methanol was evaporated from the reaction mixture and H2O was added, washed with diethyl ether. Aqueous layer was acidified to pH 4 using 10% HCl solution and extracted with ethyl acetate. The organic layer was washed with H2O, brine & dried over sodium sulphate, filtered and concentrated to give 0.75 g of crude product. The crude product was purified by column chromatography (Silica gel, Chloroform Methanol) gradient elution from 95:5 to 90:10 to give pure {[4-(3-sec-Butyl-4-hydroxy-phenoxy)-3,5-dichloro-phenyl]-ethoxycarbonyl-amino}-acetic acid. (0.125 g, 18% yield)

Workup

  1. additionwas added
  2. customMethanol was evaporated from the reaction mixture and H2O
  3. additionwas added
  4. washwashed with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with H2O, brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give 0.75 g of crude product
  11. customThe crude product was purified by column chromatography (Silica gel, Chloroform Methanol) gradient elution from 95:5 to 90:10

Sources & evidence

ORD record
ord-e11572c737aa4cf59ca57c21d885ec06
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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