Isobutyronitrile → (4S,5S)-N-cyclopropyl-2-isopropyl-4-benzyl-4,5-dihydro-1,3-oxazole-5-carboxamide

HRID 1173774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173774
[CH:1]1([NH:4][C:5]([C@@H:7]2[C@@H:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8]2)=[O:6])[CH2:3][CH2:2]1.[C:17](#[N:21])[CH:18]([CH3:20])[CH3:19].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH:1]1([NH:4][C:5]([C@H:7]2[O:8][C:17]([CH:18]([CH3:20])[CH3:19])=[N:21][C@H:9]2[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:6])[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 6559IsobutyronitrileHCID 516892Sodium BicarbonateHCID 59203389(2S,3R)-3-benzyl-2-oxiranecarboxylic cyclopropylamide

Produkt 1

HCID 59203393(4S,5S)-N-cyclopropyl-2-isopropyl-4-benzyl-4,5-dihydro-1,3-oxazole-5-carboxamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

(2S,3R)-3-Benzyl-2-oxiranecarboxylic cyclopropylamide (50 mg) and isobutyronitrile (2 ml) were mixed, and the mixture was cooled to 5° C. Boron trifluoride diethyl ether complex (2.5 equivalents) was gradually added, and the mixture was stirred at 5 to 20° C. for 2 hours. A mixture solution of ethyl acetate (10 ml) and saturated aqueous solution of sodium hydrogencarbonate (5 ml) was kept cooled at 5° C., and the reaction mixture was gradually added thereinto dropwise. The aqueous layer was removed, and then the solvent was evaporated away under reduced pressure to obtain the title compound as a brown solid (63 mg, yield: 96%).

Aufarbeitung

  1. additionBoron trifluoride diethyl ether complex (2.5 equivalents) was gradually added
  2. additionthe reaction mixture was gradually added
  3. customThe aqueous layer was removed
  4. customthe solvent was evaporated away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-039f8cf280294c74b2105a52a4431312
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834190B2

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