Water → 1-(4-Chlorobenzyl)-3-methanesulfonyloxymethyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

HRID 922734Notes

Reaction equation

HRID 922734 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9][CH2:8][C:7]([CH2:11][OH:12])([CH3:10])[C:6]1=[O:13])=[O:4].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:9][CH2:8][C:7]([CH2:11][O:12][S:30]([CH3:29])(=[O:32])=[O:31])([CH3:10])[C:6]1=[O:13])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 672540121-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 20 ml of methylene chloride, 1.00 g of Compound 2-1 obtained in Production Example 1 was dissolved. To the solution thus obtained, 0.68 ml of triethylamine and 0.324 ml of methanesulfonyl chloride were added. Thereafter, the resulting mixture was stirred at room temperature for 1.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethyl acetate was then carried out. The organic layer thus extracted was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was then purified by silica gel column chromatography to obtain 1.141 g of Compound 3-1-1.

Workup

  1. dissolutionwas dissolved
  2. customTo the solution thus obtained
  3. additionwas added to the reaction solution
  4. customthus obtained
  5. extractionextraction with ethyl acetate
  6. extractionThe organic layer thus extracted
  7. washwas washed with an aqueous solution of sodium hydrogen carbonate and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled away
  10. customthe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-57fd8d32773a433581df866046c387e7
Source dataset
uspto-grants-2016_03
Patent number
US09278966B2

Reaction notes

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