Water → [3-(2,2-Dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid

HRID 490792Notes

Reaction equation

HRID 490792 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[N:7]([CH2:16][C:17]([O:19]CC)=[O:18])[N:6]=1)=[O:4].O.[OH-].[Na+]>CO>[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[N:7]([CH2:16][C:17]([OH:19])=[O:18])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 57675509Ethyl [3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetate

Product 1

HCID 57675531[3-(2,2-Dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.30 g ethyl [3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetate from the Step D above in 20 mL MeOH and 2 mL water was added 0.50 mL of 5 N NaOH solution. After the solution was stirred at room temperature for 16 hours, the solvents were removed under reduced pressure. The residue was partitioned between cold water and EtOAc with 3 mL 1 N HCl. Separate the layers. Extract the aqueous layer with EtOAc (4×). The combined EtOAc extract was washed with saturated brine (2×), dried over anhydrous Na2SO4, and evaporated to give the title compound as yellowish solid. 1H NMR (CDCl3, 500 MHz) δ 8.27 (d, J=8.9 Hz, 1H), 7.00 (dd, =2.1 & 8.9 Hz, 1H), 6.68 (d, =2.1 Hz, 1H), 5.21 (s, 2H), 3.90 (s, 3H), 1.50 (s, 9H). LC-MS: 3.40 min. (m/Z=245.1, 291.1).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was partitioned between cold water and EtOAc with 3 mL 1 N HCl
  3. customSeparate the layers
  4. extractionExtract the aqueous layer with EtOAc (4×)
  5. extractionThe combined EtOAc extract
  6. washwas washed with saturated brine (2×)
  7. dry with materialdried over anhydrous Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-c4e123806a544e21910af5adee1a5472
Source dataset
uspto-grants-2009_05
Patent number
US07528163B2

Reaction notes

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