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

HRID 352577Notes

Reaction equation

HRID 352577 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 1N 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 1N 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-2bc846603ad64781b9c8dccc5b32b7f6
Source dataset
uspto-grants-2004_06
Patent number
US06747054B2

Reaction notes

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