Sodium Hydroxide → 5-(6-Carboxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-yloxy)-pyridine-2-carboxylic acid

HRID 1177139Notes

Reaction equation

HRID 1177139 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:20]3[CH2:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=3[CH:18]=[C:17]([C:26]([O:28]C)=[O:27])[CH:16]=2)=[CH:10][N:9]=1)=[O:7])(C)(C)C.[OH-].[Na+]>CO.C1COCC1>[C:26]([C:17]1[CH:16]=[C:15]([O:14][C:11]2[CH:12]=[CH:13][C:8]([C:6]([OH:7])=[O:5])=[N:9][CH:10]=2)[C:20]2[CH2:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=2[CH:18]=1)([OH:28])=[O:27]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 595603535-(6-Methoxycarbonyl-2,2-dimethyl-2,3-dihydro-benzofuran-4-yloxy)-pyridine-2-carboxylic acid tert-butyl ester

Product 1

HCID 595601385-(6-Carboxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-yloxy)-pyridine-2-carboxylic acidYield 124.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(6-methoxycarbonyl-2,2-dim ethyl-2,3-dihydro-benzofuran-4-yloxy)-pyridine-2-carboxylic acid tert-butyl ester (163a) (110 mg, 0.275 mmol) in 2 mL MeOH and 1 mL THF was added 1N aqueous NaOH (0.55 mL, 0.55 mmol). The mixture was stirred at room temperature overnight, heated at 60° C. for 6 hr, then concentrated, acidified to pH˜3 with 1N aqueous HCl, extracted with 3×EtOAc, dried over Na2SO4, and concentrated to give 113 mg white solid. LCMS for C17H15NO6 m/z 330.00 (M+H+).

Workup

  1. temperatureheated at 60° C. for 6 hr
  2. concentrationconcentrated
  3. extractionextracted with 3×EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d123a7e7ee3a4c33976a38d3feb14857
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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