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

HRID 1250376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250376
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c29b058e2493427a88269b633004e531
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06337403B1

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