Methanesulfonic Acid → Methanesulfonic acid 3-(4-chlorobenzyl)-1-methyl-2-oxo-cyclopentylmethyl ester

HRID 922737Notes

Reaction equation

HRID 922737 reaction equation
COC([C:5]1([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:9][CH2:8][C:7]([CH2:11][O:12][S:13]([CH3:16])(=[O:15])=[O:14])([CH3:10])[C:6]1=[O:17])=O.CS(O)(=O)=O>O>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][CH:5]2[CH2:9][CH2:8][C:7]([CH2:11][O:12][S:13]([CH3:16])(=[O:15])=[O:14])([CH3:10])[C:6]2=[O:17])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 867182541-(4-Chlorobenzyl)-3-methanesulfonyloxymethyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

Product 1

HCID 86718257Methanesulfonic acid 3-(4-chlorobenzyl)-1-methyl-2-oxo-cyclopentylmethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

To 1.26 g of Compound 3-1-1 obtained in Production Example 2, 0.255 ml of methanesulfonic acid and 88.3 mg of water were added, and the resulting mixture was stirred at 110° C. for 3.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethyl acetate was then carried out. The extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled away.

Workup

  1. additionwere added
  2. additionwas added to the reaction solution
  3. customthus obtained
  4. extractionextraction with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine
  6. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-4834d1e3a0d24272b1d1ff11bbc6667e
Source dataset
uspto-grants-2016_03
Patent number
US09278966B2

Reaction notes

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