m-Chloroperbenzoic acid → 2-(3-Chloro-4-methanesulfonyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl ester

HRID 2214104Notes

Reaction equation

HRID 2214104 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:16]1[CH:21]=[CH:20][C:19](SC)=[C:18]([Cl:24])[CH:17]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][C:8]2([O:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH2:7]1.Cl[C:27]1C=C(C=CC=1)C(OO)=O.C(=O)(O)[O-].[Na+].[S:42](=[O:45])(O)[O-:43].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([S:42]([CH3:27])(=[O:45])=[O:43])=[C:18]([Cl:24])[CH:17]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][C:8]2([O:11][CH2:12][CH2:13][CH2:14][O:15]2)[CH2:7]1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 67482163HCID 67482163, compound

Product 1

HCID 674820872-(3-Chloro-4-methanesulfonyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-chloro-4-methylsulfanyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl ester (1.18 g, 3.07 mmol) in methylene chloride (8 mL) cooled to 0° C. was slowly treated with a mixture of 3-chloroperoxybenzoic acid (˜70%, 1.51 g based on 70%, 6.13 mmol) and sodium bicarbonate (1.03 g, 12.26 mmol) in methylene chloride (8 mL). The thick reaction mixture was diluted with methylene chloride (8 mL) and was then allowed to warm to 25° C., where it was stirred for 4 h. The reaction mixture was diluted with methylene chloride (200 mL) and water (200 mL). The organic phase was cooled down to 0° C. and then slowly treated with a saturated aqueous sodium bisulfite solution (200 mL). The organic layer was washed with a saturated aqueous sodium bicarbonate solution (100 mL), water (100 mL), and a saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl ester (1.22 g, 95%) as a colorless oil: EI-HRMS m/c calcd for C19H25ClO6S (M)+ 416.1060 found 416.1054.

Workup

  1. temperatureThe organic phase was cooled down to 0° C.
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution (100 mL), water (100 mL)
  3. dry with materiala saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5185c75bb05540b09f50c2fadfdc0e70
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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