4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 23, Pages 8151-8153

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo048686r

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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.

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