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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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Amidines as amide bond replacements in VLA-4 antagonists

Theodore M Kamenecka1, You-Jung Park, Linus S Lin

  • 1Department of Medicinal Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA. theodore.kamenecka@merck.com

Bioorganic & Medicinal Chemistry Letters
|April 15, 2004
PubMed

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Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
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Amides to Amines: LiAlH4 Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.