Water → HCID 46174362, compound

HRID 709173Notes

Reaction equation

HRID 709173 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-3c2e8b6bb79247db8f9aa9101037d0e3
Source dataset
uspto-grants-2015_11
Patent number
US09180119B2

Reaction notes

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