Dimethylformamide → (R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl ester

HRID 19194Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19194
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][O:10][CH:9]1[CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].[N+:31]([C:34]1[CH:38]=CN[N:35]=1)([O-:33])=[O:32].[CH3:39][N:40]([CH3:43])C=O>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:39][N:40]2[CH:43]=[CH:38][C:34]([N+:31]([O-:33])=[O:32])=[N:35]2)[CH2:11][O:10][C:9]1([CH3:13])[CH3:25])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86635235Toluene-4-sulfonyloxymethyl-oxazolidine-3-carboxylic acid t-butyl esterHCID 178526745HCID 178526745, Verbindung

Produkt 1

HCID 57920020(R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl esterAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred mixture of (S)-2,2-dimethyl-4-(toluene-4-sulfonyloxymethyl-oxazolidine-3-carboxylic acid t-butyl ester (2.20 g, 5.71 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (0.93 g, 6.73 mmol) and 3-nitro-1H-pyrazole (prepared as in Example 5, 0.59 mg, 5.20 mmol). After addition was complete the mixture was stirred at 60° C. for 18 h. The reaction mixture was diluted with ethyl acetate, washed with water followed by a saturated sodium chloride solution and dried over magnesium sulfate. The organic layer was concentrated, and the crude product was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 100% ethyl acetate/hexanes) to afford (R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl ester (1.21 g, 65%) as a colorless oil: LR-ES-MS m/z calculated for C14H22N4O5 [M]+ 326, observed 327 [M+H]+.

Aufarbeitung

  1. additionAfter addition
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic layer was concentrated
  5. customthe crude product was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-35d5750b182c46519ed7608834d5ac46
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741327B2

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