Diethyl Ether → (S)-2-(4-nitrophenyl)-1-[(thiophen-2-yl)oxazol-4-yl]ethanamine HBr

HRID 424896

Reaktionsgleichung

Reaktionsgleichung von HRID 424896
[Br:1][CH2:2][C:3](=O)[C@@H:4]([NH:15]C(=O)OC(C)(C)C)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[C:29]([NH2:31])=[O:30].C(OCC)C>CC#N>[BrH:1].[N+:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C@@H:4]([C:3]2[N:31]=[C:29]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)[O:30][CH:2]=2)[NH2:15])=[CH:11][CH:10]=1)([O-:14])=[O:13]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 220632-ThiophenecarboxamideHCID 53778469(S)-tert-Butyl (4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-yl)carbamate

Produkt 1

HCID 66704762(S)-2-(4-nitrophenyl)-1-[(thiophen-2-yl)oxazol-4-yl]ethanamine HBr

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of (S)-tert-butyl 4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-ylcarbamate, 7, (38.7 g, 100 mmol), and thiophene-2-carboxamide (14 g, 110 mmol) (available from Alfa Aesar) in CH3CN (500 mL) is refluxed for 5 hours. The reaction mixture is cooled to room temperature and diethyl ether (200 mL) is added to the solution. The precipitate which forms is collected by filtration. The solid is dried under vacuum to afford the desired product which can be used for the next step without purification.

Aufarbeitung

  1. temperatureis refluxed for 5 hours
  2. filtrationThe precipitate which forms is collected by filtration
  3. customThe solid is dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9f04e2b395b34f0ea6772242bf09a346
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106078B2

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