Methanol → Methyl 4-nitro-L-phenylalaninate hydrochloride

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Reaction Steps

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).

Provenance & Evidence