792864-20-1

Basic information

• Product Name: N-phthalimido-4-(bis-2-chloroethyl)amino-L-phenylalanine ethyl ester
• Synonyms: N-phthalimido-4-(bis-2-chloroethyl)amino-L-phenylalanine ethyl ester
• CAS NO: 792864-20-1
• Molecular Weight: 463.361
• Mol File: 792864-20-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-phthalimido-4-(bis-2-chloroethyl)amino-L-phenylalanine ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-phthalimido-4-(bis-2-chloroethyl)amino-L-phenylalanine ethyl ester(792864-20-1)
• EPA Substance Registry System: N-phthalimido-4-(bis-2-chloroethyl)amino-L-phenylalanine ethyl ester(792864-20-1)

Safety Data

• Hazardous Substances Data: 792864-20-1(Hazardous Substances Data)

Upstream product

• 36097-39-9 (S)-methyl 2-acetamido-3-(4-nitrophenyl)propanoate 
• 147065-06-3 L-nitrophenylalanine hydrochloride 
• 34276-53-4 ethyl (S)-2-amino-3-(4-nitrophenyl)propionate 
• 74743-23-0 N-phthalimido-4-amino-L-phenylalanine ethyl ester 
• 97338-02-8 N-phthalimido-4-(bis-2-hydroxyethyl)amino-L-phenylalanine ethyl ester 
• 555-16-8 4-nitrobenzaldehdye 
• 624-70-4 1-chloro-2-iodoethane 
• 17451-67-1 N-phthalimido-4-nitro-L-phenylalanine ethyl ester 

Downstream Products

• 112117-81-4 4-[bis-(2-chloro-ethyl)-amino]-L-phenylalanine ethyl ester; hydrochloride 
• 3223-07-2 melphalan hydrochloride 

Relevant articles and documents

A PROCESS FOR THE SYNTHESIS OF MELPHALAN

The invention relates to a process for the preparation of Melphalan (4-[bis(2-5 chloroethyl)amino]-L-phenylalanine of formula (I) said process comprising the reaction of a 4-amino-L-phenylalanine protected at the carboxy and amino aminoacidic groups with an agent able to convert the aromatic amino group into a group of formula: -N(CH2CH2OS(O)nO-)2, wherein n is 1 or 2 followed by conversion of the –-N(CH2CH2OS(O)nO-)2 group into a -N(CH2CH2Cl)2 group. The invention also provides novel intermediates useful for the preparation of Melphalan.

Synthesis method of melphalan

The invention discloses a synthesis method of melphalan. The synthesis method comprises the following steps: (a), carrying out a reduction reaction: taking a compound which has a structure shown as aformula I as a raw material, and carrying out reduction reaction on the compound, a catalyst and hydrogen to obtain a reduction product shown in formula I, wherein in the formula I, X represents one of oxygen or nitrogen; R1 represents one of hydrogen, saturated alkyl group or unsaturated alkyl group; R2 and R3 respectively represent one of the hydrogen, alkyl carbonyl, amino carbonyl or alkoxycarbonyl; carrying out alkylation reaction on an alkylating reagent and the obtained reduction product in the presence of an acid binding agent to obtain an alkylated product; carrying out hydrolysis reaction on the alkylated product in acid or alkali; after concentrating, adjusting a pH value, extracting, washing and carrying out salification in dried alcohol or ester solvents of hydrochloric acid;then refining with acetonitrile to obtain melphalan hydrochloride. The synthesis method of the melphalan, disclosed by the invention, has the advantages of high yield in each step, simple operation, mild reaction conditions, no high-toxic or high-corrosion reagent, high purity of the obtained product and suitability for industrialized production.