HCID 67176053, compound → HCID 46179476, compound

HRID 238413Notes

Reaction equation

HRID 238413 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[C:13]3[C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:32])[NH2:31])=[CH:26][C:25]=3[CH3:33])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>CO.O>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:13]3[C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:32])[NH2:31])=[CH:26][C:25]=3[CH3:33])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 67176053HCID 67176053, compound

Product 1

HCID 46179476HCID 46179476, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 3-(1-(4-(1H-imidazol-1-yl)phenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)propanoate (25 mg, 0.057 mmol) and LiOH monohydrate (42 mg, 1 mmol) in a mixture of methanol (1.5 mL) and water (0.5 mL), and the reaction mixture was stirred at room temperature overnight. Methanol was removed under reduced pressure, and the residue was diluted with water (5 mL), and the aqueous layer was washed with ethyl acetate (5 mL×3). The aqueous layer was adjusted to PH=6˜7 with 1N HCl, and the resulting mixture was extracted with a mixture of dichloromethane and isopropanol (3:1, 5 mL×3). The combined organic layer was dried, and evaporated to give 3-(1-(4-(1H-imidazol-1-yl)phenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)propanoic acid, (5-4, R1=1H-imidazol-1-yl) (12 mg, yield: 51%) as a yellow solid.

Workup

  1. customMethanol was removed under reduced pressure
  2. additionthe residue was diluted with water (5 mL)
  3. washthe aqueous layer was washed with ethyl acetate (5 mL×3)
  4. extractionthe resulting mixture was extracted with a mixture of dichloromethane and isopropanol (3:1, 5 mL×3)
  5. customThe combined organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-aa3c92f53b844ab683251691d07618d7
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

Loading…