Potassium Permanganate → (2R)-2-[3-Chloro-4-(methanesulfonyl)phenyl]-3-(2-oxocyclopentyl)propanoic acid

HRID 2214074Notes

Reaction equation

[Mn]([O-])(=O)(=O)=[O:2].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C@@H:17]([CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])[C:18]([OH:20])=[O:19])[CH:11]=[CH:12][C:13]=1[S:14]([CH3:16])=[O:15]>O.CO>[Cl:7][C:8]1[CH:9]=[C:10]([C@@H:17]([CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])[C:18]([OH:20])=[O:19])[CH:11]=[CH:12][C:13]=1[S:14]([CH3:16])(=[O:2])=[O:15]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of potassium permanganate (101 mg, 0.64 mmol) in water (1.83 mL) was treated with a solution of 2(R)-(3-chloro-4-methanesulfinyl-phenyl)-3-(2-oxo-cyclopentyl)-propionic acid (191.5 mg, 0.58 mmol) in methanol (5.8 mL). The reaction was stirred at 25° C. for 1 h. At this time, the reaction was diluted with methanol and then was filtered through a pad of celite. The filtrate was concentrated in vacuo and was azeotroped with acetonitrile. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 90/10 methylene chloride/methanol with glacial acetic acid) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(2-oxo-cyclopentyl)-propionic acid (87 mg, 43%) as an off-white foam: EI-HRMS m/e calcd for C15H17ClO5S (M−H2O)+ 326.0379, found 326.0378.

Workup

filtrationwas filtered through a pad of celite
concentrationThe filtrate was concentrated in vacuo
customwas azeotroped with acetonitrile

Sources & evidence

ORD record: ord-2ef21b6c03eb497aa7d47320d756ec74
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105671B2

Reaction notes

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