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Synthesis of 4‐^13^C‐4‐hydroperoxycyclophosphamide and alpha‐^13^C‐4‐hydroperoxycyclophosphamide by Chorng-Kei Ho; Susan M. Ludeman is a Medicine article available to read on EtoBox.
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## 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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- Author
- Chorng-Kei Ho; Susan M. Ludeman
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0022-2135)
- Published
- 1990
- Language
- EN
- Field
- Medicine (Life Sciences)