Water → (3-Isobutyryl-6-methoxy-1H-indazol-1-yl)acetic acid

HRID 229459Notes

Reaction equation

HRID 229459 reaction equation
[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]([O:20]CC)=[O:19])[N:7]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].O.[OH-].[Na+]>CO>[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]([OH:20])=[O:19])[N:7]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86618180Ethyl (3-isobutyryl-6-methoxy-1H-indazol-1-yl)acetate

Product 1

HCID 57675517(3-Isobutyryl-6-methoxy-1H-indazol-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 1.68 g ethyl (3-isobutyryl-6-methoxy-1H-indazol-1-yl)acetate in 50 mL MeOH at 45° C. Add 10 mL water and 1.5 mL 5 N NaOH solution. The resulting mixture was heated overnight and evaporated to dry. The residue was taken up in water, acidified with 0.8 mL concentrated HCl, and extracted with 3×50 mL EtOAc. The combined organic extract was washed with water and saturated brine, dried over anhydrous Na2SO4, and evaporated to give the title compound as a white solid. 1H NMR (CDCl3, 500 MHz) δ 8.27 (d, 8.9 Hz, 1H), 7.01 (dd, 2.1 & 8.9 Hz, 1H), 6.69 (d, 2.1 Hz, 1H), 5.23 (s, 2H), 3.91 (s, 3H), 3.85 (heptet, 6.9 Hz, 1H), 1.28 (d, 7.1 Hz, 6H). In NOE difference spectrum, irradiation of the 5.23 ppm singlet showed positive NOE at the 6.69 ppm doublet. LC-MS: 2.94 min. (m/Z=277.0, 299.0).

Workup

  1. temperatureThe resulting mixture was heated overnight
  2. customevaporated
  3. customto dry
  4. extractionextracted with 3×50 mL EtOAc
  5. extractionThe combined organic extract
  6. washwas washed with water and saturated brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-14041b0b5df149d19cb5c3194a02768d
Source dataset
uspto-grants-2009_07
Patent number
US07563816B2

Reaction notes

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