Hydrochloric Acid → 2-(3-Chloro-4-methylsulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid methyl ester

HRID 854836Notes

Reaction equation

HRID 854836 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([Cl:26])[CH:17]=1)[CH2:5][CH:6]1[CH2:15][CH2:14][C:9]2(OCC[O:10]2)[CH2:8][CH2:7]1.Cl>CC(C)=O.O>[CH3:1][O:2][C:3](=[O:27])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([Cl:26])[CH:17]=1)[CH2:5][CH:6]1[CH2:15][CH2:14][C:9](=[O:10])[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 674821112-(3-Chloro-4-methylsulfonyl-phenyl)-3-(1,4-dioxa-spiro[4.5]dec-8-yl)-propionic acid methyl ester

Product 1

HCID 674821092-(3-Chloro-4-methylsulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid methyl esterYield 100.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-chloro-4-methylsulfonyl-phenyl)-3-(1,4-dioxa-spiro[4.5]dec-8-yl)-propionic acid methyl ester (667 mg, 1.60 mmol) in acetone (15 mL) was treated with a 10% aqueous hydrochloric acid solution (1.8 mL). The reaction mixture was stirred at 25° C. for 24 h. The reaction mixture was then diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford pure 2-(3-chloro-4-methylsulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid methyl ester (600 mg, 100%) as a colorless gum which was used without further purification: EI-HRMS m/e calcd for C17H21ClO5S (M+Na)+ 395.0690. found 395.0692.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34b6078a6cfb4e9fbf08e358e4bedde1
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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