Ethanol → Ethyl 4-nitro-3-phenyl-L-alaninate monohydrochloride

HRID 1817692Notes

Reaction equation

HRID 1817692 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:18])=O.[CH2:20](O)[CH3:21]>>[ClH:18].[CH2:20]([O:12][C:11](=[O:13])[C@H:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)[NH2:10])[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 137064-Nitro-3-phenyl-L-alanineHCID 24386Thionyl Chloride

Product 1

HCID 6453710Ethyl 4-nitro-3-phenyl-L-alaninate monohydrochloride

Procedure

4-nitrophenylalanine (5 g, 1 eq, mmol) was added in portions to a solution of dry ethanol (50 mL) and thionylchloride (5 mL) at −5° C. It was stirred at that temperature for another one hour, followed by stirring at RT for 16 h. The reaction mixture was condensed on rotavapour, azeotroped with toluene, and then dried over high vaccum pump to obtain 4-nitrophenylalanine ethyl ester hydrochloride as white solid (quantitative yield).

Workup

  1. stirringby stirring at RT for 16 h
  2. customcondensed on rotavapour
  3. customazeotroped with toluene
  4. customdried over high vaccum pump

Sources & evidence

ORD record
ord-632f3edea4054839bcb43bc975ee78ea
Source dataset
uspto-grants-2009_10
Patent number
US07598293B2

Reaction notes

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