Ethyl 2-(4-(3,4-dimethoxybenzyloxy)-3-chlorobenzamido)-5-phenoxybenzoate → 2-(4-(3,4-Dimethoxybenzyloxy)-3-chlorobenzamido)-5-phenoxybenzoic acid

HRID 2099961Notes

Reaction equation

HRID 2099961 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:6][O:7][C:8]1[CH:34]=[CH:33][C:11]([C:12]([NH:14][C:15]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][C:16]=2[C:17]([O:19]CC)=[O:18])=[O:13])=[CH:10][C:9]=1[Cl:35]>C1COCC1.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:6][O:7][C:8]1[CH:34]=[CH:33][C:11]([C:12]([NH:14][C:15]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][C:16]=2[C:17]([OH:19])=[O:18])=[O:13])=[CH:10][C:9]=1[Cl:35]

Participants

5

Reactant 1

HCID 57796889Ethyl 2-(4-(3,4-dimethoxybenzyloxy)-3-chlorobenzamido)-5-phenoxybenzoate

Product 1

HCID 577968912-(4-(3,4-Dimethoxybenzyloxy)-3-chlorobenzamido)-5-phenoxybenzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1C (160 mg, 0.29 mmol) in THF (30 mL) and MeOH (10 mL) at 0° C. was treated with a solution of LiOH monohydrate (60 mg, 1.42 mmol) in water (10 mL). The resulting solution was stirred for 16 hours, and then concentrated to 10 mL. The resulting suspension was taken up in water (10 mL) and brought to pH 5 with 1 N HCl. The solution was extracted with EtOAc (4×25 mL), dried (Na2SO4), filtered and concentrated to afford the 1D as a white solid. (130 mg, 84%).

Workup

  1. concentrationconcentrated to 10 mL
  2. extractionThe solution was extracted with EtOAc (4×25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ff6af964ef47478a9bf4887ea6f908e9
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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