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

HRID 2249579Notes

Reaction equation

HRID 2249579 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-d899ea73723646ffa3614f7d692e309a
Source dataset
uspto-grants-2008_01
Patent number
US07314889B2

Reaction notes

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