Methanesulfonyl chloride → HCID 54026786, compound

HRID 257332Notes

Reaction equation

HRID 257332 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]([C:10]1([F:16])[CH2:14][CH2:13][CH2:12][CH:11]1[OH:15])=[O:9]>N1C=CC=CC=1>[CH3:6][O:7][C:8]([C:10]1([F:16])[CH2:14][CH2:13][CH2:12][CH:11]1[O:15][S:2]([CH3:1])(=[O:4])=[O:3])=[O:9]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19783080HCID 19783080, compound

Product 1

HCID 54026786HCID 54026786, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

0.36 g (3 mmol) of methanesulfonyl chloride was added under ice cooling to a mixture of 0.5 g (3 mmol) of 1-fluoro-2-hydroxy-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 2a) synthesized in Example 1 and 2 ml of pyridine, and the mixture was stirred at 0° C. for 5 hours. The reaction solution was poured into a ice water and extracted with ether, and the ether layer was washed with cold water. The ether layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to obtain 0.59 g (yield: 80%) of the desired 2-methanesulfonyloxy-1-fluoro-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 5a).

Workup

  1. extractionextracted with ether
  2. washthe ether layer was washed with cold water
  3. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-65e058ee9350440a8f8311daf2430717
Source dataset
uspto-grants-1993_11
Patent number
US05262385

Reaction notes

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