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

HRID 641169Notes

Reaction equation

HRID 641169 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 and the resulting mixture was extracted with 60 ml of ethyl acetate twice. The organic layer was concentrated and chromatographed (methanol/dichloromethane 5:100) to give 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 extracted with 60 ml of ethyl acetate twice
  3. concentrationThe organic layer was concentrated
  4. customchromatographed (methanol/dichloromethane 5:100)

Sources & evidence

ORD record
ord-d6571dc37f704435b71e688d917ccc43
Source dataset
uspto-grants-2010_04
Patent number
US07696198B2

Reaction notes

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