METHOD OF PRODUCING ADAMANTYLALKYL AND ADAMANTYLOXYALKYL ETHERS OF TOSYLOXYMETHYL-PHOSPHONIC ACID Russian patent published in 2012 - IPC C07F9/40 

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing adamantylalkyl and adamantyloxyalkyl ethers of tosyloxymethyl-phosphonic acid of formula

,

used in synthesis of pharmaceutical preparations having antiviral activity, from compounds of formula , where X is absent, R=H, R'=H, n=1; or X is absent, R=H, R'=H, n=2; or X is absent, R=H, R'=CH₃, n=1; or X=O, R=H, R'=H, n=2; or X=O, R=C₂H₅, R'=H, n=2; Ts denotes tosyl (n-toluene sulphonyl). The method involves treatment of a solution of O,O-diethyl(tosyloxymethyl)phosphonate in methylene chloride with bromotrimethylsilane, followed by reaction of the formed bis-trimethylsilyl ether with oxalyl chloride in the presence of catalytic amounts of N,N-dimethylformamide in ratio of 3 mole oxalyl chloride to 1 mole O,O-diethyl(tosyloxymethyl)phosphonate. The formed dichlorophosphonate is then treated with two equivalents of alcohols of formula II in the presence of Et₃N.

EFFECT: method with improved reaction selectivity and use of readily available reagents simplifies and reduces cost of production.

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