Sodium Hydroxide → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-(hydroxymethyl)-2-methyl-3-phenylpropanoic acid

HRID 563439Notes

Reaction equation

HRID 563439 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:18]([CH2:24][OH:25])([CH3:23])[C:19]([O:21]C)=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:18]([CH2:24][OH:25])([CH3:23])[C:19]([OH:21])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59252864methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-(hydroxymethyl)-2-methyl-3-phenylpropanoate

Product 1

HCID 670057973-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-(hydroxymethyl)-2-methyl-3-phenylpropanoic acidYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-(hydroxymethyl)-2-methyl-3-phenylpropanoate (121 mg, 0.29 mmol) was dissolved in MeOH (10 mL) and treated with 1 M NaOH (10 mL). After stirring overnight, the MeOH was removed in vacuo, the residue acidified with conc HCl to pH 4-5 and extracted with EtOAc×3. The organic layer was dried with MgSO4, filtered, concentrated in vacuo to give 115 mg (98%) of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-(hydroxymethyl)-2-methyl-3-phenylpropanoic acid. MS found: (M+H)+=405.

Workup

  1. customthe MeOH was removed in vacuo
  2. extractionextracted with EtOAc×3
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3e4fcee5983483299db5a6b5022d624
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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