Sodium Hydroxide → HCID 11386125, compound

HRID 494365Notes

Reaction equation

HRID 494365 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[N:26]=[C:27]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:28][C:29]=3[CH3:30])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[N:8][N:9]([CH2:11][CH3:12])[CH:10]=1)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[CH2:11]([N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[C:7]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][C:25]3[N:26]=[C:27]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:28][C:29]=3[CH3:30])=[CH:21][CH:22]=2)(=[O:16])=[O:15])=[N:8]1)[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11386673HCID 11386673, compound2×

Product 1

HCID 11386125HCID 11386125, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the title compound of Example 2, 1-ethyl-3-{4-[5-methyl-2-phenyl-oxazol-4-ylmethoxy]-benzenesulfonylamino}-1H-pyrazole-4-carboxylic acid ethyl ester (0.09 g, 0.18 mmol) in dioxane (4 mL) is added 2N sodium hydroxide (4 mL) at RT. The reaction mixture is stirred for 4 days. The reaction mixture is acidified with ice-cold 2 N hydrochloric acid (HCl) and placed in an ice bath for 1 h. The solid formed is separated, washed with water and dried under vacuum. The product, 1-ethyl-3-{4-[5-methyl-2-phenyl-oxazol-4-ylmethoxy]-benzenesulfonylamino}-1H-pyrazole-4-carboxylic acid is obtained as a white solid: MS [m/z] 481.1 [M-1]−.

Workup

  1. waitplaced in an ice bath for 1 h
  2. customThe solid formed
  3. customis separated
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-545da03f6ca84838ae8033b7ead7b48e
Source dataset
uspto-grants-2009_05
Patent number
US07538135B2

Reaction notes

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