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Citation: LIU Xiao-Ling, LIN Shu-Ying, SHENG Shou-Ri, XIN Qin, SONG Cai-Sheng. Synthesis of 3-Amino-2-hydroxy-4-phenylbutanoic Acid[J]. Chinese Journal of Applied Chemistry, ;2005, 22(2): 222-223. shu

Synthesis of 3-Amino-2-hydroxy-4-phenylbutanoic Acid

1.
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027

Corresponding author: SHENG Shou-Ri,
Received Date: 30 March 2004
Available Online: 30 September 2004
Fund Project: 江西省教育厅科技项目(赣财教[2003]73号)资助 (赣财教[2003]73号)

3-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.
- Bestatin,
- aminohydroxyphenylbutanoic acid,
- synthesis
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