223431-83-2

Basic information

• Product Name: N-(N-benzyloxycarbonyl-L-pyroglutamyl)-p-bis(2-hydroxyethyl)amino-L-phenylalanine benzyl ester
• CAS NO: 223431-83-2
• Molecular Weight: 603.672
• Mol File: 223431-83-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(N-benzyloxycarbonyl-L-pyroglutamyl)-p-bis(2-hydroxyethyl)amino-L-phenylalanine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(N-benzyloxycarbonyl-L-pyroglutamyl)-p-bis(2-hydroxyethyl)amino-L-phenylalanine benzyl ester(223431-83-2)
• EPA Substance Registry System: N-(N-benzyloxycarbonyl-L-pyroglutamyl)-p-bis(2-hydroxyethyl)amino-L-phenylalanine benzyl ester(223431-83-2)

Safety Data

• Hazardous Substances Data: 223431-83-2(Hazardous Substances Data)

Upstream product

• 40291-26-7 N-benzyloxycarbonyl-L-pyroglutamic acid N-hydroxysuccinimido ester 
• 184684-97-7 N-tert-butyloxycarbonyl-p-bis(2-hydroxyethyl)amino-L-phenylalanine benzyl ester 
• 127977-25-7 benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-(4'-nitrophenyl)propionate 

Downstream Products

• 223431-91-2 N-(N-benzyloxycarbonyl-L-pyroglutamyl)-p-bis(2-chloroethyl)amino-L-phenylalanine benzyl ester 

Relevant articles and documents

Synthesis of α-aminoacyl derivatives of melphalan for use in antibody directed enzyme pro-drug therapy

L-Alanyl-, D-alanyl-, L-prolyl-, L-pyroglutamyl- and D- phenylalanylmelphalan were synthesized in 8 steps, with the reactive nitrogen mustard moiety formed at the penultimate step. After protection of p- nitrophenylalanine with benzyl ester and N-t-butyloxycarbonyl (BOC) groups, the aromatic nitro was reduced to an amine which was reacted with ethylene oxide to give a product with a bis(2-hydroxyethyl)amino moiety. After removal of BOC, it was coupled to the relevant N-benzyloxycarbonyl-α-amino acid. Chlorination of hydroxyethyl yielded the bis(2-chlorethyl)amino compound. Final removal of protecting groups was by catalytic hydrogenolysis.