Sodium Hydroxide → 4-(3-(2-(3-Hydroxy-4-phenylbutyl)-5-oxopyrrolidin-1-yl)propyl)benzoic acid

HRID 1267425Notes

Reaction equation

HRID 1267425 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH:21]([OH:29])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[OH:29][CH:21]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:20][CH2:19][CH:14]1[CH2:15][CH2:16][C:17](=[O:18])[N:13]1[CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:30])=[O:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 129700864-{3-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzoic acid methyl ester

Product 1

HCID 113268964-(3-(2-(3-Hydroxy-4-phenylbutyl)-5-oxopyrrolidin-1-yl)propyl)benzoic acidYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{3-[2-(3-hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzoic acid methyl ester (2.28 g, 5.57 mmol) in MeOH (20 mL) was added 2N NaOH (5 mL). The reaction mixture was stirred at room temperature for 20 h and was heated under reflux for 3 h. The volatiles were removed in vacuo and the residue was diluted with CH2Cl2 and 1 N HCl. The aqueous solution was extracted with CH2Cl2 (2×) and the combined organic extracts were washed with brine. The organic solution was dried (MgSO4), filtered and concentrated to yield the title compound (2.03 g). 1H NMR (CDCl3) δ7.98 (d, 2H), 7.34-7.18 (m, 7H), 3.80 (m, 1H), 3.67 (m, 1H), 3.58 (m, 1H), 2.97 (m, 1H), 2.81 (m, 1H), 2.68 (m, 3H), 2.45-2.27 (m, 2H), 2.13-1.30 (m, 9H); MS 396.3 (M+1), 394.2 (M−1).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customThe volatiles were removed in vacuo
  4. additionthe residue was diluted with CH2Cl2 and 1 N HCl
  5. extractionThe aqueous solution was extracted with CH2Cl2 (2×)
  6. washthe combined organic extracts were washed with brine
  7. dry with materialThe organic solution was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ffd681022fe34790ba054512fbf34caa
Source dataset
uspto-grants-2003_04
Patent number
US06552067B2

Reaction notes

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