Study On The Synthesis Of Anti-Aids Drug Navir Intermediate

This thesis describes the synthesis of the (2S,3S)-1,2-Epoxy-3-(tert-butoxy carbonylamino)-4-phenylbutane, Which is the key intermediate of navir series. For example the Saquinavir, Ritonavir, Amprenavir. Navir is an anti-AIDS-protease inhibitors. So it is important for the synthesis of its intermediate. It can reduce the pains of the AIDS patients and extend the life of the AIDS patient.In this thesis, an approach to the synthesis of (2S,3S)-1,2-epoxy-3-(tert-butoxycarbonylamino)-4-phenylbutane has been developed. Using L-phenylalanine as the starting material,(2S,3S)-1,2-epoxy-3-(tert-butoxycarbonylamino)-4-phenylbutane was prepared through amino protection, diazomethane reaction, chlorination, reduction and cyclization in an overall yield of60.6%. The chloroalcohol intermediate was synthesized by MPV reduction using alumimum alkoxides as reducing reagent. This route has its advantage in high stereoslecting and yield. And it is suitable for the industrial production. There is a high practical value for the commercial production of protease inhibitors.In conclusion, this synthetic method has some advantages such as cheap available material, mild reaction conditions, high yield and simple operation, which is suitable for the large-scale production. Products and various related impurity was characterized by IR,1H-NMR was confirmed.