Sodium Hydroxide → HCID 68557117, compound

HRID 1967586Notes

Reaction equation

HRID 1967586 reaction equation
C([O:3][C:4](=[O:37])[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]([C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[CH:21]=2)=[C:14]([Cl:36])[CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])C.[OH-].[Na+]>CO.O>[Cl:18][C:16]1[CH:17]=[C:12]([N:6]([CH2:5][C:4]([OH:37])=[O:3])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:13]=[C:14]([Cl:36])[C:15]=1[O:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([C:27](=[O:35])[C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)[CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68554419HCID 68554419, compound

Product 1

HCID 68557117HCID 68557117, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The ester (2.27 g, 4.0 mmol) was dissolved in MeOH (14 mL) and to that solution of NaOH (0.48 g, 12 mmol) in H2O (7 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. The aqueous layer was acidified to pH 4 using 10% HCl solution and extracted with ethyl acetate The organic layer was washed with water, brine, dried over sodium sulphate, filtered and concentrated to give pure product ({3,5-Dichloro-4-[3-(4-chloro-benzoyl)-4-hydroxy-phenoxy]-phenyl}-ethoxycarbonyl-amino)-acetic acid. (1.7 g, 79% 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 The organic layer
  6. washwas washed with water, brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4894ef1f554849cb87857e06eaa7074f
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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