Hydrochloric Acid → 3-[4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzoic acid

HRID 1819359Notes

Reaction equation

HRID 1819359 reaction equation
C([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[CH:17]=3)[CH2:13][C:12]2=[O:30])[CH:6]=1)C.[OH-].[Na+].Cl>CCO.O>[CH:25]1([O:24][C:18]2[CH:17]=[C:16]([CH:14]3[CH2:15][N:11]([C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:4]([OH:31])=[O:3])[C:12](=[O:30])[CH2:13]3)[CH:21]=[CH:20][C:19]=2[O:22][CH3:23])[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688284533-[4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzoic acid ethyl ester

Product 1

HCID 688305433-[4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

3-[4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzoic acid ethyl ester (180 mg, 0.43 mmol) was mixed with EtOH:water (1:1, 20 mL) and NaOH (1N, 1.3 mL). The mixture was heated to 90° C. for 12 h and then cooled down to r.t. After neutralizing to pH=2 with HCl (1N), the mixture was extracted twice with EtOAc. The organic layer was combined, washed with brine and dried over MgSO4. After concentration 150 mg of the desired product was obtained as a light brown solid. Yield: 89%.

Workup

  1. temperaturecooled down to r.t
  2. extractionthe mixture was extracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-4abb232e50fe409bbe0c5207de512756
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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