Title: Synthesis of 3-Amino-2-hydroxy-4-phenylbutanoic Acid
Abstract: Amino-2-hydroxy-4-phenylbutanoic acid(compound 3), the key intermediate for the synthesis of Bestatin, was prepared via substitution, condensation and reduction in an overall yield of about 47.8%. The reaction of nitromethane with benzyl bromide in the presence of sodium ethoxide gave a 82% yield of 1-nitro-2-phenylethane(compound 1). The condensation of compound 1 with glyoxylic acid monohydrate in sodium ethoxide/ethanol afforded a 72% yield of 3-nitro-2-hydroxy-4-phenylbutyric acid(compound 2), which was hydrogenated to compound 3 with a 81% yield in acetic acid in the presence of Pd/C. All the compounds were characterized by 1H NMR, IR and elemental analysis.
Publication Year: 2005
Publication Date: 2005-01-01
Language: en
Type: article
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