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ChemicalBook CAS DataBase List Melphalan
148-82-3

Melphalan synthesis

5synthesis methods
Melphalan, L-3-[p-[bis-(2-chloroethyl)amino]phenyl]alanine (30.2.1.13), is a structural analog of chlorambucil in which the butyric acid fragment is replaced with an aminoacid fragment, alanine. This drug is synthesized from L-phenylalanine, the nitration of which with nitric acid gives 4-nitro-L-phenylalanine (30.2.1.8). Reacting this with an ethanol in the presence of hydrogen chloride gives the hydrochloride of 4-nitro-L-phenylalanine ethyl ester (30.2.1.9), the amino group of which is protected by changing it to phthalamide by a reaction with succinic anhydride to give 30.2.1.10. The nitro group in this molecule is reduced to an amino group using palladium on calcium carbonate as a catalyst. The resulting aromatic amine (30.2.1.11) is then reacted with ethylene oxide, which forms a bis-(2- hydroxyethyl)-amino derivative (30.2.1.12). The hydroxy groups in this molecule are replaced with chlorine atoms upon reaction with thionyl chloride, after which treatment with hydrochloric acid removes the phthalamide protection, giving melphalan (30.2.13).

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Yield:-

Steps:

Multi-step reaction with 3 steps
1.1: sodium carbonate / acetonitrile / 2 h / 23 - 85 °C / Large scale
2.1: trichlorophosphate / Isopropyl acetate / 2.5 h / 40 - 50 °C / Inert atmosphere
3.1: hydrogenchloride; water / Isopropyl acetate / 12 h / Reflux
3.2: pH 2

References:

FARMABIOS S.P.A.;POZZOLI, Claudio Gianluca;CANEVARI, Valentina;CURTI, Matteo WO2014/191426, 2014, A1

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