Solid phase synthesis of 3-(5′-carboxypentyl)-5-substituted tetrahydro-2H-1,3,5-thiadiazin-2-thione derivatives

The solid phase synthesis of 3-(5-carboxypentyl)-5-substituted tetrahydro-2H-1,3,5-thiadiazin-2-thione derivatives 5 is described. 6-Amino-n-hexanoic acid was attached via its C-terminal to hydroxymethyl polystyrene using a 'SASRIN' linker The bound amino acid was converted to the corresponding dithiocarbamate 3 followed by cyclization in the presence of formaldehyde and the corresponding free amino acids to afford 3-(5'-carboxypentyl)5-substituted tetrahydro-2H-1,3,5-thiadiazin-2-thiones 4. The final products were cleaved from the resin and obtained in moderate yields. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.