Sodium Hydroxide → HCID 9807167, compound

HRID 1354177Notes

Reaction equation

HRID 1354177 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH:30][C:31](=[O:38])[CH2:32][CH2:33][C:34]([O:36]C)=[O:35])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:20]([C:21]3[CH:22]=[CH:23][C:24]([S:27]([NH:30][C:31](=[O:38])[CH2:32][CH2:33][C:34]([OH:36])=[O:35])(=[O:28])=[O:29])=[CH:25][CH:26]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:17])[F:18])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21104428HCID 21104428, compound

Product 1

HCID 9807167HCID 9807167, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[({4-[2-(3-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]phenyl}sulfonyl)amino]-4-oxobutanoate (0.1 g 0.1 8 mmol) in methanol (20 ml) was heated under reflux with 2M sodium hydroxide (0.45 ml 0.9 mmol) for 24 hr. The solvent was removed and the resulting solid was dissolved in water (20 ml) and the pH was adjusted to 2 with 2M hydrochloric acid. The liberated solid was extracted into ethyl acetate (3×20 ml) and the combined extracts were washed with water (20 ml) and brine (20 ml). Drying (MgSO4) and removal of solvent gave the title compound as a white solid (0.09 g 92%). MH+: 536

Workup

  1. customThe solvent was removed
  2. dissolutionthe resulting solid was dissolved in water (20 ml)
  3. extractionThe liberated solid was extracted into ethyl acetate (3×20 ml)
  4. washthe combined extracts were washed with water (20 ml) and brine (20 ml)
  5. customDrying
  6. custom(MgSO4) and removal of solvent

Sources & evidence

ORD record
ord-bcbde09484e340e1ad815e156543ccfb
Source dataset
uspto-grants-2007_05
Patent number
US07223772B1

Reaction notes

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