Methanol → tert-butyl N-[2-(1,2,4-oxadiazol-3-yl)propan-2-yl]carbamate

HRID 927468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927468
[NH2:1]/[C:2](=[N:14]\[OH:15])/[C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:5])[CH3:4].[CH2:16](OC(OCC)OCC)C.FC(F)(F)C(O)=O.CO>C(#N)C.O>[O:15]1[CH:16]=[N:1][C:2]([C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])([CH3:5])[CH3:4])=[N:14]1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 31214Ethyl orthoformateHCID 61324195tert-butyl N-[1-(N'-hydroxycarbamimidoyl)-1-methylethyl]carbamate

Produkt 1

HCID 73357654tert-butyl N-[2-(1,2,4-oxadiazol-3-yl)propan-2-yl]carbamateAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of (Z)-tert-butyl 1-amino-1-(hydroxyimino)-2-methylpropan-2-ylcarbamate (Example 33 b, 2 g, 9.2 mmol) in acetonitrile (10 mL) was added triethoxymethane (CAN 122-51-0, 4.8 mL) and trifluoroacetic acid (CAN 76-05-1, 0.1 mL). The mixture was heated to 50° C. and stirred overnight. The reaction mixture was added to methanol (10 mL) and water (10 mL). After evaporation of solvents, the residue was purified by column chromatography (silica gel, 60 g, eluting with 30% to 50% ethyl acetate in petroleum ether) to give the target product (0.668 g, 32%) MS (EI): m/e=250.1 [M+H]+.

Aufarbeitung

  1. customAfter evaporation of solvents
  2. customthe residue was purified by column chromatography (silica gel, 60 g, eluting with 30% to 50% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-487f9c0ca488478f92fa929f95992bd7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290451B2

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