Methanol → Methyl 4-nitro-L-phenylalaninate hydrochloride

HRID 280039

Reaction equation

HRID 280039 reaction equation
S(Cl)([Cl:3])=O.[N+:5]([C:8]1[CH:19]=[CH:18][C:11]([CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH3:20]O>>[ClH:3].[CH3:20][O:16][C:15](=[O:17])[C@H:13]([CH2:12][C:11]1[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:19][CH:18]=1)[NH2:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 137064-Nitro-3-phenyl-L-alanine2×HCID 24386Thionyl Chloride

Product 1

HCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

Procedure

In an adaptation of the method of Guttman and Boissonnas [Helv. Chem. Acta, 41, 1852-1867 (1958)], thionyl chloride (distilled, 0.69 ml, 9.5 mmol) was added dropwise to methanol (20 ml at -10° C.). p-Nitro-L-phenylalanine (compound 1, 1.00 g, 4.76 mmol) was added, and the solution was stirred 24 hours. After evaporating to dryness the residue was recrystallized from methanol/ether giving 1.00 g (81%) of a white solid melting at 218°-219° C.; [α]D25 =+11.5° (c=0.9, H2O).

Workup

  1. customAfter evaporating to dryness the residue
  2. customwas recrystallized from methanol/ether giving 1.00 g (81%) of a white solid melting at 218°-219° C.
  3. custom[α]D25 =+11.5° (c=0.9, H2O)

Sources & evidence

ORD record
ord-d0d037781d184f2b8a40f2255a5a5052
Source dataset
uspto-grants-1986_05
Patent number
US04587046

Linked notes

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