Water → HCID 67460966, compound

HRID 469730Notes

Reaction equation

HRID 469730 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][CH2:12][C@H:11]2[C:16](=[O:27])[NH:17][C:18]2[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:20][N:19]=2)[CH:5]=1.[OH-].[Na+].O>CO>[C:23]([C:21]1[O:20][N:19]=[C:18]([NH:17][C:16]([C@@H:11]2[CH2:12][CH2:13][C:14](=[O:15])[N:10]2[C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:28])=[O:2])=[O:27])[CH:22]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 46843507HCID 46843507, compound

Product 1

HCID 67460966HCID 67460966, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[(S)-2-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-5-oxo-pyrrolidin-1-yl]-benzoic acid methyl ester (870 mg, 2.23 mmol) in methanol (30 mL) a 2 M solution of sodium hydroxide in water (5 mL, 10 mmol) is added at room temperature. After 18 h solvent is evaporated in vacuo, the concentrate is cooled in an ice-bath and acidified to pH 2 using 1 N sulfuric acid. Precipitated white solid is filtered, washed with water and dried to give the title compound, ESI m/z 372 [M+H]+.

Workup

  1. customAfter 18 h solvent is evaporated in vacuo
  2. temperaturethe concentrate is cooled in an ice-bath
  3. customPrecipitated white solid
  4. filtrationis filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-4672c9485f8c40efb0fde9b658055f88
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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