444667-48-5

Upstream product

• 288-32-4 1H-imidazole 
• 101582-69-8 4--O-benzylphenol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 51388-20-6 4-benzyloxyaniline hydrochloride 

Downstream Products

• 444667-49-6 4-[N,N-bis(2-(tert-butyldimethylsilyloxy)ethyl)amino]phenol 
• 156079-90-2 di-tert-butyl <<<4-amino>phenyl>oxy>carbonyl>-L-glutamate 
• 156079-89-9 di-tert-butyl <<<4-phenyl>oxy>carbonyl>-L-glutamate 
• 156079-01-5 di-tert-butyl <<<4-phenyl>oxy>carbonyl>-L-glutamate 
• 156079-88-8 N-{4-[N,N-bis(2-iodoethyl)amino]-phenoxycarbonyl}-L-glutamic Acid 
• 444667-51-0 di-tert-butyl N-{4-[N,N-bis(2'-(tert-butyldimethylsilyloxy)ethyl)amino]phenoxycarbonyl}-L-glutamate 
• 444667-50-9 C₂₃H₄₂ClNO₄Si₂ 

Relevant academic research and scientific papers

A higher yielding synthesis of the clinical prodrug ZD2767P using di-protected 4-[N,N-bis(2-hydroxyethyl)amino]phenyl chloroformate

A novel synthesis is described of the prodrug ZD2767P (in Phase I/II clinical trials) that improves the overall yield from 13% to 45%. The method involves the synthesis of 4-[N,N-bis(2-hydroxyethyl)amino]phenyl chloroformate protected as the bis-silyl ether, coupled with di-tert-butyl glutamate. There are clear advantages of this method compared to the literature procedure.

Methods of chemical systhesis of phenolic nitrogen mustard prodrugs

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: X2 is a halo group, and is —F, —Cl, —Br, or —I; n is an integer