Hydrochloric Acid → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone-1-acetic acid

HRID 731763Notes

Reaction equation

HRID 731763 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[CH2:19][N:18]([CH2:20][C:21]([O:23]C)=[O:22])[C:17](=[O:25])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].Cl.O>CO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][N:18]([CH2:20][C:21]([OH:23])=[O:22])[C:17](=[O:25])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 68683776HCID 68683776, compound

Product 1

HCID 236146844-(3-Cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone-1-acetic acidYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (4S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone-1-acetate (250 mg, 0.72 mmol) was treated with 8 mL of a 1M solution of potassium hydroxide in 95% methanol. After 10 hours, the reaction solution was acidified with 2N HCl to pH 3, and 30 mL of water was added. The resulting mixture was then extracted with ethyl acetate (2×60 mL) and the organic layer was concentrated. Chromatographic purification (methanol/dichloromethane 5:100) afforded 242 mg (quantitative yield) of 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone-1-acetic acid: 1H NMR (300 MHz, CDCl3) δ 6.85-73 (m, 3H), 4.84-4.74 (m, 1H), 4.20 (d, J=12.0 Hz, 1H), 4.12 (d, J=12.0, 1H), 3.82 (s, 4H), 3.66-3.46 (m, 2H), 2.89 (dd, J=16.8, 8.7 Hz, 1H), 2.58 (dd, J=16.8, 8.4 Hz, 1H), 2.00-1.72 (b, 6H), 1.70-1.50 (b, 2H).

Workup

  1. additionwas added
  2. extractionThe resulting mixture was then extracted with ethyl acetate (2×60 mL)
  3. concentrationthe organic layer was concentrated
  4. customChromatographic purification (methanol/dichloromethane 5:100)

Sources & evidence

ORD record
ord-93d2fd4e9e574252a315eee251c89fb4
Source dataset
uspto-grants-2009_09
Patent number
US07585882B2

Reaction notes

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