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

HRID 705555Notes

Reaction equation

HRID 705555 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-a116757117794e1c89ec8403b203edd8
Source dataset
uspto-grants-2015_11
Patent number
US09174950B2

Reaction notes

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