Hydrochloric Acid → (R)-4-[3-fluoro-4-(4-hydroxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1804039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804039
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:38])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C@H:25]([CH2:26][O:27]C(=O)C4C=CC=CC=4)[CH2:24][O:23][C:22]3=[O:36])=[C:17]([F:37])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.[Cl-].[Na+]>C(COC)OC.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:38])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C@H:25]([CH2:26][OH:27])[CH2:24][O:23][C:22]3=[O:36])=[C:17]([F:37])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 54755120(R)-4-[4-(4-benzoyloxymethyl-2-oxooxazolidin-3-yl)-3-fluoro-benzoyl]piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 58484618(R)-4-[3-fluoro-4-(4-hydroxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl esterAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(R)-4-[4-(4-Benzoyloxymethyl-2-oxooxazolidin-3-yl)-3-fluoro-benzoyl]piperazine-1-carboxylic acid tert-butyl ester (1.45 g) described in Preparation Example 91 was dissolved in dimethoxyethane, 4N aqueous sodium hydroxide solution was added and the mixture was stirred at room temperature. Under ice-cooling, the reaction mixture was neutralized with 1N hydrochloric acid, ethyl acetate and sodium chloride were added and the mixture was extracted with ethyl acetate, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (859 mg).

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (chloroform:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-2aa30956c3dd4c6393c4192bef09a111
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354401B2

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