Method for the synthesis of pyrrole and imidazole carboxamides on a solid support

A method for preparing a polyamide containing N-methyl 4-imidazolecarboxamide and N-methyl-pyrrolecarboxamide comprising:

• (a) sequentially adding amino acids with an amino group protected with tert-butoxycarbonyl or 9-fluorenylmethylcarbonyl and a carboxy group that has been reacted to form an activated ester or a symmetric anhydride to an amino substituted solid support, beginning with the carboxy terminal amino acid, thereby forming a polyamide having a protected amino acid;
• (b) deprotecting the amino terminal protected amino acid of the polyamide;
• and
• (c) removing the polyamide from the solid support.

A method for preparing a cyclic polyamide on a solid support comprising:

• (a) preparing a resin for attachment of the polyamide;
• (b) reacting the resin with a protected allyl ester pyrrole monomer having the following structure:
• ##STR31## (c) reacting an amino acid with reagents to provide an amino group which is protected and a carboxyl reactive with an amino functionality;
• (d) sequentially adding the protected and reactive amino acids to the solid support beginning with the carboxy terminal amino acid, thereby forming the desired polyamide;
• (e) removing the allyl ester with a Pd catalyst;
• (f) cleaving the polyamide from the resin;
• and
• (g) cyclizing and purifying the cyclized polyamide.

A method for preparing a polyamide containing N-methyl imidazolecarboxamide and N-methyl-pyrrolecarboxamide on a solid support comprising:

• (a) preparing an amino substituted polystyrene resin solid support for attachment of the polyamide;
• (b) protecting the amino group of an amino acid with a member of the group consisting of tert-butoxycarbonyl or 9-fluorenylmethylcarbonyl and reacting the carboxyl group to form the oxybenztriazole ester or a symmetric anhydride;
• (c) sequentially deprotecting the amino acid and adding the protected amino acids to the solid support beginning with the carboxy terminal amino acid, thereby forming the desired polyamide;
• (d) cleaving the polyamide from the resin by hydrogenolysis;
• and
• (e) purifying the polyamide.