74743-23-0

Basic information

• Product Name: 4-Amino-L-phenyl-N-phthalylalanine ethyl ester
• Synonyms: ethyl (S)-alpha-[(4-aminophenyl)methyl]-1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetate;(L)-ethyl 3-(4-aminophenyl)-2-(1,3-dioxoisoindolin-2-yl)propanoate;4-Amino-L-phenyl-N-phthalylalanine ethyl ester;Ethyl 3-(4-aminophenyl)-2-(1,3-dioxoisoindol-2-yl)propanoate;(S)-α-[(4-Aminophenyl)methyl]-1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetic acid ethyl ester;3-(4-aminophenyl)-2-(1,3-diketoisoindolin-2-yl)propionic acid ethyl ester;ethyl 3-(4-azanylphenyl)-2-(1,3-dioxoisoindol-2-yl)propanoate;ethyl(S)-α-[(4-aMinophenyl)Methyl]-1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetate
• CAS NO: 74743-23-0
• Molecular Formula: C₁₉H₁₈N₂O₄
• Molecular Weight: 338.35722
• EINECS: 277-979-8
• Mol File: 74743-23-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 102-103 °C(Solv: water (7732-18-5); methanol (67-56-1))
• Boiling Point: 534.8 °C at 760 mmHg
• Flash Point: 277.2 °C
• Appearance: /
• Density: 1.331 g/cm³
• Vapor Pressure: 1.64E-11mmHg at 25°C
• Refractive Index: 1.637
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.42±0.10(Predicted)
• CAS DataBase Reference: 4-Amino-L-phenyl-N-phthalylalanine ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-L-phenyl-N-phthalylalanine ethyl ester(74743-23-0)
• EPA Substance Registry System: 4-Amino-L-phenyl-N-phthalylalanine ethyl ester(74743-23-0)

Safety Data

• Hazardous Substances Data: 74743-23-0(Hazardous Substances Data)

Usage

General Description

4-Amino-L-phenyl-N-phthalylalanine ethyl ester is a chemical compound that belongs to the class of esters. It is composed of an amino group, a phenyl group, a phthalyl group, and an ethyl ester group attached to the amino acid L-phenylalanine. 4-Amino-L-phenyl-N-phthalylalanine ethyl ester is commonly used in pharmaceutical research and drug development, particularly in the synthesis of potential new drugs. Its unique structure makes it a valuable building block in the creation of novel bioactive compounds with potential therapeutic applications. Additionally, this chemical may also have potential uses in academic research, particularly in the study of protein interactions and the development of new tools for chemical biology.

InChI:InChI=1/C19H18N2O4/c1-2-25-19(24)16(11-12-7-9-13(20)10-8-12)21-17(22)14-5-3-4-6-15(14)18(21)23/h3-10,16H,2,11,20H2,1H3/t16-/m0/s1

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 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 
• 17451-66-0 N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine 
• 85-44-9 phthalic anhydride 
• 207569-25-3 p-nitro-L-phenylalanine hydrate 
• 93963-19-0 N-(2-carboxy-benzoyl)-4-nitro-L-phenylalanine ethyl ester 
• 17451-67-1 N-phthalimido-4-nitro-L-phenylalanine ethyl ester 

Downstream Products

• 102312-93-6 4-(2-chloro-ethylamino)-L-phenylalanine ethyl ester 
• 101288-75-9 4-benzylamino-L-phenylalanine 
• 51447-20-2 4-[benzyl-(2-chloro-ethyl)-amino]-L-phenylalanine 
• 116604-57-0 4-(2-hydroxy-ethylamino)-N,N-phthaloyl-L-phenylalanin-ethyl ester 
• 123153-20-8 4-benzylamino-N,N-phthaloyl-L-phenylalanin-ethyl ester 
• 97338-02-8 N-phthalimido-4-(bis-2-hydroxyethyl)amino-L-phenylalanine ethyl ester 
• 792864-20-1 N-phthalimido-4-(bis-2-chloroethyl)amino-L-phenylalanine ethyl ester 
• 3223-07-2 melphalan hydrochloride 
• 123080-67-1 4-benzylidenamino-N,N-phthaloyl-L-phenylalanin-ethyl ester 
• 116604-67-2 4-ethylamino-N,N-phthaloyl-L-phenylalanin-ethyl ester 
• 118871-22-0 N,N-phthaloyl-4-propylamino-L-phenylalanin-ethyl ester 

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.