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

HRID 1046619Notes

Reaction equation

HRID 1046619 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (S)-tert-butyl 4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-ylcarbamate, 7, (38.7 g, 100 mmol), and thiophen-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.

Workup

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

Sources & evidence

ORD record
ord-0cbfc135b4fb4a058883c01607c90c7b
Source dataset
uspto-grants-2013_10
Patent number
US08569348B2

Reaction notes

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