Water → 3-Cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid methyl ester

HRID 1355023Notes

Reaction equation

HRID 1355023 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:11]1[CH:16]=[CH:15][C:14](Cl)=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:22][S:23]([O-:25])=[O:24].[Na+].C(OCC)(=O)C.O>CS(C)=O>[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:23]([CH3:22])(=[O:25])=[O:24])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2733271Sodium methanesulfinateHCID 12069506Methyl 4-chloro-α-(cyclopentylmethyl)-3-nitrobenzeneacetate

Product 1

HCID 120695073-Cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid methyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-(4-chloro-3-nitrophenyl)-3-cyclopentyl-propionic acid methyl ester (1.00 g, 3.21 mmol) and sodium methanesulfinate (0.36 g, 3.53 mmol) in dimethyl sulfoxide (3 mL) was heated at 130° C. for 5 h. The black reaction mixture was then poured over ice (20 g), resulting in the formation of a brown sticky substance. The resulting mixture was then treated with ethyl acetate (50 mL) and water (50 mL), and the layers were separated. The aqueous layer was further extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid methyl ester (0.95 g, 84%) as a yellow gel: FAB-HRMS m/e calcd for C16H21NO6S (M+H)+ 356.1169, found 356.1175.

Workup

  1. customThe black reaction mixture
  2. customresulting in the formation of a brown sticky substance
  3. customthe layers were separated
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-255356c08fdc4a7d8289adf7c5f08872
Source dataset
uspto-grants-2007_05
Patent number
US07223868B2

Reaction notes

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