Hydrogen Peroxide → 2-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid

HRID 1265447Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1SC.OO.O1CCC[CH2:23]1.[S:27]([O-:30])([O-])=[O:28].[Na+].[Na+]>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH2:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[S:27]([CH3:23])(=[O:30])=[O:28]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-(3-chloro-4-methylsulfanyl-phenyl)-3-cyclopentyl-propionic acid (4.14 g, 13.85 mmol) in formic acid (7.08 mL) was cooled to 0° C. and then treated with a 30% aqueous hydrogen peroxide solution (7.85 mL). Tetrahydrofuran (4 mL) was added to help solubilize the starting material. The resulting reaction mixture was allowed to warm to 25° C. where it was stirred at this temperature overnight. The reaction mixture was then cooled to 0° C. and slowly treated with a saturated aqueous sodium sulfite solution. The product was extracted into ethyl acetate (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (4.54 g, 99.1%) as a white solid: mp 123.9-126.2° C.; FAB-HRMS m/e calcd for C15H19ClO4S (M+H)+ 331.0771, found 331.0776.

Workup

customThe resulting reaction mixture
temperatureto warm to 25° C. where it
temperatureThe reaction mixture was then cooled to 0° C.
extractionThe product was extracted into ethyl acetate (3×20 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ab85d9333f574e33bb2f68a47d9e8e44
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545155B2

Reaction notes

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