Methanesulfonyl chloride → (2R,3R)-2-(2,3-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol

HRID 1250376Notes

Reaction equation

HRID 1250376 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[C@:14]([OH:20])([C@H:17]([OH:19])[CH3:18])[CH2:15][OH:16].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[C@:14]([OH:20])([C@H:17]([O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH3:18])[CH2:15][O:16][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69944031(2R,3R)-2-(2,3-difluorophenyl)-1,2,3-butanetriol

Product 1

HCID 86757716(2R,3R)-2-(2,3-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanolYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.71 g (50 mmol) of methanesulfonyl chloride were added to a solution of 3.51 g (16.1 mmol) of (2R,3 R)-2-(2,3-difluorophenyl)-1,2,3-butanetriol [obtained as described in Step 7(ii) above] in 18 ml of pyridine at 0° C. After stirring the resulting mixture for 0.5 hours, saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the product was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and then washed with aqueous sodium chloride solution and then concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel (100 g) column using a 1:1 mixture of ethyl acetate and hexane as the eluant to afford 5.04g (yield 84%) of the title compound as a colorless oil.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with dilute hydrochloric acid
  3. washwashed with aqueous sodium chloride solution
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography on a silica gel (100 g) column
  6. additiona 1:1 mixture of ethyl acetate and hexane as the eluant

Sources & evidence

ORD record
ord-c29b058e2493427a88269b633004e531
Source dataset
uspto-grants-2002_01
Patent number
US06337403B1

Reaction notes

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