Methods of chemical systhesis of phenolic nitrogen mustard...

Details Methods of chemical systhesis of phenolic nitrogen mustard... Methods of chemical systhesis of phenolic nitrogen mustard...

2005-07-12

2005-07-12

Richter, Johann (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C560S155000, C560S190000, C562S590000

Reexamination Certificate

active

06916949

ABSTRACT:
This invention pertains to novel methods for the synthesis of certain nitrogen mustard prodrugs, such as N-{4-[N,N-bis(2-haloethylamino)-phenoxycarbonyl}-L-glutamic acid:wherein: X2is a halo group, and is —F, —Cl, —Br, or —I; n is an integer from 0 to 4; and, each RAis an aryl substituent. The methods comprise, at least, the steps of: glutamate conjugation (GC); silyloxy deprotection (SD); and, sulfonic esterification (SU). Certain preferred methods comprise the steps of: amine substitution (AS); silyloxy protection (SP); phenolic deprotection (PD); activation (AC); glutamate conjugation (GC); silyloxy deprotection (SD); sulfonic estenfication (SU); halogenation (HL); glutamate deprotection (GD); and glutamic acid protection (GP).

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