Sodium Hydroxide → {4-Chloro-2-[5-chloro-2-(1-methyl-2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzyl]-phenoxy}-acetic acid

HRID 2244476Notes

Reaction equation

HRID 2244476 reaction equation
C([O:8][C:9](=[O:37])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[CH2:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[O:27][CH:28]([CH3:36])[C:29](=[O:35])[N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)C1C=CC=CC=1.[OH-].[Na+]>CO>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:9]([OH:37])=[O:8])=[C:13]([CH2:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=2[O:27][CH:28]([CH3:36])[C:29](=[O:35])[N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68452258{4-Chloro-2-[5-chloro-2-(1-methyl-2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzyl]-phenoxy}-acetic acid benzyl ester

Product 1

HCID 11961250{4-Chloro-2-[5-chloro-2-(1-methyl-2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzyl]-phenoxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution comprising {4-chloro-2-[5-chloro-2-(1-methyl-2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzyl]-phenoxy}-acetic acid benzyl ester (63 mg, 0.116 mmol) in MeOH (1 mL) is treated with 2 M NaOH (145 μL) and allowed to stir at RT overnight. The resulting suspension is filtered, dissolved in water (1 mL) and the pH of the solution is adjusted to pH 1 using 2 M HCl. A precipitate forms which is filtered and dried in a vacuum oven to afford the titled product; MH+=452.

Workup

  1. filtrationThe resulting suspension is filtered
  2. dissolutiondissolved in water (1 mL)
  3. filtrationA precipitate forms which is filtered
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-3df06150a36144d5a7666398daaff108
Source dataset
uspto-grants-2010_03
Patent number
US07678826B2

Reaction notes

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