Sodium Hydroxide → 3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid

HRID 1685533Notes

Reaction equation

HRID 1685533 reaction equation
C[C:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)([CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4].[OH-].[Na+]>CO>[CH:7]1([CH2:6][CH:2]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[C:3]([OH:5])=[O:4])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67215757HCID 67215757, compound

Product 1

HCID 120694893-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-cyclopentyl-2-(4-methanesulfonylphenyl)propionic acid (2.8 g, 9.0 mmol), 1 N sodium hydroxide (19 mL), and methanol (25 mL) was stirred at room temperature for 24 h. The reaction mixture was concentrated in vacuo to remove the methanol and 2 N HCl (9 mL) was slowly added at 0° C. to give white crystals of 3-cyclopentyl-2-(4-methanesulfonylphenyl)propionic acid. Yield: 2.3 g (87%). mp: 160-161° C. 1H-NMR (CDCl3, δ ppm): 7.90 (d, J=8.2 Hz, 2H); 7.54 (d, J=8.2 Hz, 2H); 3.72 (t, J=7.8 Hz, 1H); 3.05 (s, 3H); 2.15-2.08 (m, 1H); 1.9-1.45 (m, 8H); 1.05-1.20 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove the methanol and 2 N HCl (9 mL)
  3. additionwas slowly added at 0° C.

Sources & evidence

ORD record
ord-9ccc9bd0c1e847f09a23e23bbe75afad
Source dataset
uspto-grants-2012_04
Patent number
US08148412B2

Reaction notes

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