Acyloxymethyl Carbonochloridates. New Intermediates in Prodrug Synthesis
作者:Michael Folkmann、Frantz J. Lund
DOI:10.1055/s-1990-27124
日期:——
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.
Describes a method for obtaining substantially pure chloromethyl chloroformate from a chloroformate mixture comprising chloromethyl chloroformate and methyl chloroformate by heating the chloroformate mixture in a reaction zone at temperatures ranging from at least 50° C. to the reflux temperature of the chloroformate mixture in the reaction zone while simultaneously removing volatile gaseous decomposition products from the reaction zone. Dichloromethyl chloroformate may also be present in the chloroformate mixture.
KINETICS OF THE PHOTOCHLORINATION OF MONOCHLOROMETHYL CHLOROFORMATE IN THE GAS PHASE
作者:M. J. Dignam、W. G. Forbes、D. J. Le Roy
DOI:10.1139/v57-178
日期:1957.11.1
The general features of the mechanism of the over-all process are similar to those for the over-all process studied previously. The reaction is inhibited by HCl. Chains are terminated by two proces...
Abstract Dichloromethyl carbonates, easily available upon treatment alcohols with dichloromethyl chloroformate, react with various amines to give carbamates in high yield under mild conditions. Extension of the reaction for the synthesis of oxazolones from 2-aminoalcohols is also demostrated.