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Synthesis of 4-13C-4-hydroperoxycyclophosphamide and alpha-13C-4-hydroperoxycyclophosphamide

✍ Scribed by Chorng-Kei Ho; Susan M. Ludeman

Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
468 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

New synthetic routes were developed for incorporating ^13^C into the oxazaphosphorine ring and nitrogen mustard functionality of cyclophosphamide metabolites. 1,2‐^13^C~2~‐Vinylbromide and ethylene oxide were used to synthesize 3,4‐^13^C~2~‐3‐butenyl N,N‐bis(2‐chloroethyl)phosphorodiamidate via the intermediacy of 3,4‐^13^C~2~‐3‐buten‐1‐ol. Ozonolysis of the phosphorodiamidate gave 4‐^13^C‐4‐hydroperoxycyclophosphamide with an overall yield of 16% which was 27‐times higher than a previously reported synthesis. As an extension of this synthetic pathway, 2‐^13^C‐ethyl bromoacetate was used to incorporate ^13^C into the C~1~ position of bis(2‐chloroethyl)amine hydrochloride which was used as a precursor to alpha‐^13^C‐4‐hydroperoxycyclophosphamide (obtained in 16% overall yield). Also discussed are applications of these pathways to the synthesis of diversely labelled (^14^C, ^13^C, ^2^H) 4‐hydroperoxycyclophosphamides, chirally‐labelled oxazaphosphorines, phosphoramide mustards, and related alkylating agents.

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