Sodium Bicarbonate → (R)-3-[2-fluoro-4-(piperazine-1-carbonyl)phenyl]-4-methoxymethyloxazolidin-2-one

HRID 1804041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804041
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C@H:25]([CH2:26][O:27][CH3:28])[CH2:24][O:23][C:22]3=[O:29])=[C:17]([F:30])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[F:30][C:17]1[CH:16]=[C:15]([C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:31])[CH:20]=[CH:19][C:18]=1[N:21]1[C@H:25]([CH2:26][O:27][CH3:28])[CH2:24][O:23][C:22]1=[O:29]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 54755121(R)-4-[3-fluoro-4-(4-methoxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 58484520(R)-3-[2-fluoro-4-(piperazine-1-carbonyl)phenyl]-4-methoxymethyloxazolidin-2-oneAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

(R)-4-[3-Fluoro-4-(4-methoxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester (506 mg) described in Preparation Example 93 was dissolved in ethyl acetate (5 mL), 4N hydrogen chloride/ethyl acetate (5 mL) was added and the mixture was stirred at room temperature. Under ice-cooling, the reaction mixture was neutralized with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, and extracted once with ethyl acetate and the aqueous layer was extracted with twice with chloroform. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound (390 mg).

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. extractionextracted once with ethyl acetate
  3. extractionthe aqueous layer was extracted with twice with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-51b2e81de1a74df5b02afdb6d60c1568
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354401B2

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