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Synthesis 1990; 1990(12): 1159-1166
DOI: 10.1055/s-1990-27124
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Acyloxymethyl Carbonochloridates. New Intermediates in Prodrug Synthesis

Michael Folkmann* , Frantz J. Lund
  • *Leo Pharmaceutical Products, DK-2750 Ballerup, Denmark
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Publikationsdatum:
02. Mai 2002 (online)

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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.