Sodium Hydroxide → HCID 178461815, compound

HRID 20547

Reaction equation

HRID 20547 reaction equation
[OH:1][CH2:2][C@H:3]([CH3:31])[O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:23]([NH:25][C:26]2[CH:30]=[CH:29][NH:28][N:27]=2)=[O:24])[CH:22]=1)[O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][CH:10]=1.[OH-].[Na+]>C1COCC1.O>[OH:1][CH2:2][C@H:3]([CH3:31])[O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:23]([NH:25][C:26]2[CH:30]=[CH:29][NH:28][N:27]=2)=[O:24])[CH:22]=1)[O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178469074HCID 178469074, compound

Product 1

HCID 178461815HCID 178461815, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-{3-[(1S)-2-hydroxy-1-methylethoxy]-5-[(1H-pyrazol-3-ylamino)carbonyl]phenoxy}benzoate (175 mg, 0.4 mmol) in THF (5 mL) and water (1 mL) was treated with 1N sodium hydroxide solution (3 mL) and the reaction stirred at RT for 16 hours. On completion, the solvent was removed in vacuo and 1N citric acid added until pH 3-4. The white precipitate was collected by filtration and dried in vacuo to give the desired product as a white solid (138 mg, 85%).

Workup

  1. customOn completion, the solvent was removed in vacuo and 1N citric acid
  2. additionadded until pH 3-4
  3. filtrationThe white precipitate was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f71922eafb5c4170ae05152f347a6481
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Linked notes

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