Acyloxymethyl Carbonochloridates. New Intermediates in Prodrug Synthesis
- 1 January 1990
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (12) , 1159-1166
- https://doi.org/10.1055/s-1990-27124
Abstract
The synthesis of a number of stable acyloxymethyl carbonochloridates 7 has been accomplished in four steps from chloromethyl carbonochloridate 3. Each step has been optimized with propanoyloxymethyl carbonochloridate 7c as a model compound (64% overall yield). Diethyl ether-boron trifluoride catalyzes the conversion of carbonothioate 6cc to the carbonochloridate 7c by chlorination with sulfuryl chloride. Acylation of a few compounds containing hydroxy or amino groups by 7c is described.Keywords
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