The Procter Gamble Company

Lawrence Joseph Wilson

David Edward Portlock

Min Li

 The subject invention involves novel acyl isothiocyanate resins of formula (I) and processes for making them: (a) starting with a phenyl carboxy resin, treating the resin with any reagent that converts the carboxy to an acyl halide, followed by treatment with tetranikylammonium thiocyanate or an alkali metal salt thereof, to provide the acyl isothiocyanate resin. The subject invention also involves processes for making guanidine compounds and related cyclized compounds using an acyl isothiocyanate resin, comprising the following steps: (b) reacting the acyl isothiocyanate resin with a primary amine; (c) reacting the product from Step (b) with a sulfur activating agent and ammonia or a primary or secondary amine; (d) treating the product from Step (c) with a strong base or medium strength acid to cleave product from the resin, providing the guanidine compound or/and the related cyclized compound.

Acyl isothiocyanate resins and their use in solid-supported synthesis of guanidines

The subject invention involves processes for making 1-aminohydantoin compounds using a solid support resin, comprising the following steps; (a) preparing a resin-bound protected &agr;-hydrazinyl ester; (1) by reacting the resin with an &agr;-bromo carboxylic acid, then with a protected hydrazine; or (2) by reacting the resin with a protected &agr;-hydrazinyl carboxylic acid; (b) preparing a resin-bound imine by removing the blocking group from the hydrazinyl moiety, then reacting the unprotected hydrazinyl moiety with an aldehyde or ketone; (c) preparing a resin-bound secondary urea: (1) by reacting the imine with p-nitrophenylchloroformate or trisphosgene, then with a primary amine; or (2) by reacting the imine with an isocyanate, and (d) preparing the 1-aminohydantoin compound by removing the secondary urea from the resin and cyclizing it.

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Mason, OH, United States of America

Lawrence Joseph Wilson