Methanesulfonyl chloride → 2,2-dichloro-1-((4S,5R)-5-(4-(6-(chloromethyl)pyridin-3-yl)phenyl)-4 (fluoromethyl)-2,2-dimethyloxazolidin-3-yl)ethanone

HRID 1500274

Reaktionsgleichung

Reaktionsgleichung von HRID 1500274
[Cl:1][CH:2]([Cl:28])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][C:21]([CH2:24]O)=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:27])[CH3:26])=[O:4].CCN(C(C)C)C(C)C.CS([Cl:42])(=O)=O>C(Cl)Cl>[Cl:28][CH:2]([Cl:1])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][C:21]([CH2:24][Cl:42])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:26])[CH3:27])=[O:4]

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 866954062,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-(6-(hydroxymethyl)pyridin-3-yl)phenyl)-2,2-dimethyloxazolidin-3-yl)ethanone

Produkt 1

HCID 867131642,2-dichloro-1-((4S,5R)-5-(4-(6-(chloromethyl)pyridin-3-yl)phenyl)-4 (fluoromethyl)-2,2-dimethyloxazolidin-3-yl)ethanoneAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a cooled (ice-water) solution of the product of step 1 (800 mg, 1.87 mmol) and DIPEA (0.675 mL, 3.75 mmol) in DCM (10 mL) is slowly added methanesulfonyl chloride (0.150 mL, 1.87 mmol). The reaction mixture is stirred at room temperature for 6 hours. The reaction is diluted with DCM (10 mL), washed with water (2×10 mL) dried over Na2SO4 and concentrated under reduced pressure to give the title compound (813 mg): LCMS m/z (Cl): 445 [M+H].

Aufarbeitung

  1. washwashed with water (2×10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-63de992dc7ad49eea645a79efe833794
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206126B2

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