Sodium Hydroxide → 3-Cyclopentyl-2-[4-(2-oxo-propylsulfonyl)-phenyl]-propionic acid

HRID 505588Notes

Reaction equation

C([O:3][C:4](=[O:25])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:21][C:22](=[O:24])[CH3:23])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[OH-].[Na+]>CO.O>[CH:7]1([CH2:6][CH:5]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH2:21][C:22](=[O:24])[CH3:23])(=[O:19])=[O:20])=[CH:14][CH:13]=2)[C:4]([OH:25])=[O:3])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of the title C compound, 3-cyclopentyl-2-[4-(2-oxo-propylsulfonyl)-phenyl]-propionic acid ethyl ester (5 g, 0.013 mol) in 40 mL of methanol and 60 mL of water is treated with 1 g (0.027 mol) of sodium hydroxide and the reaction is stirred at 25° C. for 6 h. The reaction mixture is concentrated under vacuum, and the residue is re-dissolved in water and extracted with diethyl ether (50 mL). The aqueous layer is then acidified to pH 1 with 1 N aqueous hydrochloric acid solution. This solution is extracted with ethyl acetate (2×100 mL). The organic layer is washed with water and brine, dried over sodium sulfate and then filtered and evaporated under vacuum to give 3-cyclopentyl-2-[4-(2-oxo-propylsulfonyl)-phenyl]-propionic acid as a white solid.

Workup

concentrationThe reaction mixture is concentrated under vacuum
dissolutionthe residue is re-dissolved in water
extractionextracted with diethyl ether (50 mL)
extractionThis solution is extracted with ethyl acetate (2×100 mL)
washThe organic layer is washed with water and brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated under vacuum

Sources & evidence

ORD record: ord-4714cf1d572b469c8ddff148896a5883
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781451B2

Reaction notes

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