Sodium Hydroxide → 3-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]-propanoic acid

HRID 2362198Notes

Reaction equation

HRID 2362198 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[N:8]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=2[CH3:28])[C:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)C.[OH-].[Na+]>CO>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[N:8]([C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=3[CH3:28])[C:7]([CH2:6][CH2:5][C:4]([OH:29])=[O:3])=[CH:11][CH:10]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 583056233-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester

Product 1

HCID 583057203-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]-propanoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester (36 mg, 0.09 mmol) was dissolved in 1 mL methanol. 1 N NaOH (0.18 mL, 0.18 mmol.) was added. After 18 hrs, the reaction was concentrated in vacuo and diluted with water. The pH was adjusted to 1 with 1 M HCl and extracted with EtOAc (3×4 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with hexanes and dried under high vacuum to yield 3-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]-propanoic acid (16 mg, 50%, light orange powder).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with EtOAc (3×4 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with hexanes
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-47093b56b19a49e0a5473371336e3c8d
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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