ChemicalBook CAS DataBase List Melphalan

Melphalan synthesis

5synthesis methods

Product Name:Melphalan
CAS Number:148-82-3
Molecular formula:C13H18Cl2N2O2
Molecular Weight:305.2

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).

67630-01-7 Synthesis

L-Phenylalanine, 4-aMino-N-[(1,1-diMethylethoxy)carbonyl]-, ethyl ester

67630-01-7
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148-82-3
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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

FullText

62978-52-3
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148-82-3
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References

L-Phenylalanine, 4-[bis(2-chloroethyl)amino]-N-[(1,1-dimethylethoxy)carbonyl]-, ethyl ester

189744-28-3
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148-82-3
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References

N-Boc-4-[bis(2-hydroxyethyl)amino]-L-phenylalanine Methyl Ester

1217651-06-3
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148-82-3
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References

(S)-ethyl3-(4-(bis(2-hydroxyethyl)amino)phenyl)-2-(tert-butoxycarbonylamino)propanoate

189744-27-2
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148-82-3
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References

Melphalan Related Search:

2-Aminophenol L-Phenylalanine PHENYL VALERATE Diphenyl ether D-Phenylalanine 6-Aminocaproic acid Phenyl salicylate Glycine Tris(hydroxymethyl)aminomethane Chlormethine