Water → HCID 46174362, compound

HRID 1188276Notes

Reaction equation

HRID 1188276 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH2:6][C:7]1[N:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH2:27])=[CH:22][C:21]=2[CH3:29])[C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)C.O.[OH-].[Na+]>C(O)C>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([N:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:10][CH:11]=[C:7]2[CH2:6][CH2:5][C:4]([OH:30])=[O:3])=[C:21]([CH3:29])[CH:22]=1)(=[O:28])[NH2:27]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67175307HCID 67175307, compound

Product 1

HCID 46174362HCID 46174362, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[1-(4-carbamoyl-2-methyl-phenyl)-5-(4-methoxy-phenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester (86 mg, 0.216 mmol) was dissolved in ethanol (4 mL). Water (0.5 mL) was added to the ethanolic solution followed by the addition of 1N NaOH (0.51 mL, 0.51 mmol). The reaction mixture was stirred at room temperature for 1 h and then at 45° C. for an additional hour. After removal of the solvent in vacuo, the residue was diluted with water (6 mL) and extracted with ethyl acetate (2×6 mL). The pH of the aqueous layer was adjusted to 2 with 1N HCl and then extracted with ethyl acetate (6 mL). The combined organic layer was dried over anhydrous Na2SO4 and the solvent removed in vacuo to obtain 3-[1-(4-Carbamoyl-2-methyl-phenyl)-5-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-propanoic acid as the product (68 mg, 85%).

Workup

  1. waitat 45° C. for an additional hour
  2. customAfter removal of the solvent in vacuo
  3. additionthe residue was diluted with water (6 mL)
  4. extractionextracted with ethyl acetate (2×6 mL)
  5. extractionextracted with ethyl acetate (6 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8d353c2ba1154b228597deec2af2d2e5
Source dataset
uspto-grants-2014_03
Patent number
US08673961B2

Reaction notes

Loading…