US EPA

7438738 

Journal Article 

Synthesis of N-methylpyrrole and N-methylimidazole amino acids suitable for solid-phase synthesis 

Jaramillo, D; Liu, Q; Aldrich-Wright, J; Tor, Y 

2004 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

69 

23 

8151-8153 

English 

15527311 

10.1021/jo048686r 

WOS:000225024200060 

New and higher yielding synthetic routes to N-protected N-methylpyrrole and N-methylimidazole amino acids are introduced to circumvent difficulties associated with established schemes. Key steps in each synthesis include copper-mediated cross-coupling reaction to directly install a carbamate-protected 4-amine in the N-methylpyrrole derivative and effective nitration followed by a one-pot reduction/Boc protection of the amine in the synthesis of the N-Me-imidazole amino acid. 

Amines; Chemical analysis; Copper; Derivatives; Synthesis (chemical); Chemical complexes; Coupling reaction; Synthetic routes; Amino acids; 1 methylimidazole; 1 methylpyrrole; 2 trichloroacetyl 1 methylimidazole; 2 trichloroacetyl 1 methylpyrrole; 4 bromo 2 trichloroacetyl 1 methylpyrrole; 4 nitro 2 trichloroacetyl 1 methylimidazole; carbamic acid derivative; carboxylic acid derivative; copper; imidazole derivative; methyl 1 methyl 4 nitroimidazole 2 carboxylate; methyl 4 [(tert butoxycarbonyl)amino] 1 methylimidazole 2 carboxylate; methyl 4 [(tert butoxycarbonyl)amino] 1 methylimidazole 2 carboxylic acid; methyl 4 [(tert butoxycarbonyl)amino] 1 methylpyrrole 2 carboxylate; methyl 4 [(tert butoxycarbonyl)amino] 1 methylpyrrole 2 carboxylic acid; methyl 4 bromomethylpyrrole 2 carboxylate; pyrrole derivative; unclassified drug; amino acid synthesis; article; cross coupling reaction; nitration; reduction; Amino Acids; Combinatorial Chemistry Techniques; Imidazoles; Molecular Structure; Pyrroles