Diethyl Ether → (S)-(4-ethyloxazol-2-yl)-2-(4-nitrophenyl)ethanamine

HRID 509154Notes

Reaction equation

HRID 509154 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:19](=[O:21])[NH2:20])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(C)(C)C.Br[CH2:24][C:25](=O)[CH2:26][CH3:27].C(OCC)C>CC#N>[CH2:26]([C:25]1[N:20]=[C:19]([C@@H:8]([NH2:7])[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)[O:21][CH:24]=1)[CH3:27]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 131561-Bromo-2-butanoneHCID 14134844(S)-tert-butyl 1-amino-3-(4-nitrophenyl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 59464675(S)-(4-ethyloxazol-2-yl)-2-(4-nitrophenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of [1-(S)-carbamoyl-2-(4-nitrophenyl)ethyl-carbamic acid tert-butyl ester, 1, (10 g, 32.3 mmol) and 1-bromo-2-butanone (90%, 4.1 mL, 36 mmol) in CH3CN (500 mL) is refluxed for 18 hours. The reaction mixture is cooled to room temperature and diethyl ether is added to the solution and the precipitate which forms is removed by filtration and is used without further purification.

Workup

  1. temperatureis refluxed for 18 hours
  2. customthe precipitate which forms is removed by filtration
  3. customis used without further purification

Sources & evidence

ORD record
ord-a2e1732485c74f46826717b98d156054
Source dataset
uspto-grants-2015_08
Patent number
US09096555B2

Reaction notes

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