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US 5,861,532 AGranted
Solid-phase synthesis of N-alkyl amides
AssigneeChiron Corporation
InventorsEdward G. Brown, John M. Nuss
Life of this patent
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Abstract
Methods for solid phase synthesis of N-alkyl amides comprise reductive amination of carbonyl compounds using a reducing agent and an amine-containing linker bound to a solid support. The methods afford high yields of linker-bound, monoalkylated amines, and subsequent coupling with acid derivatives provide derivatized N-substituted amides in excellent yields after cleavage from the solid-phase. Compositions useful in solid phase synthesis are also described.
Claims13
A method for the solid phase synthesis of an N-substituted amide product, comprising:
- a) providing:
- i) a carbonyl compound, ii) a linker bound to a solid support, said solid support-bound linker comprising at least one amine group, iii) a reducing agent, and iv) an aqueous solvent system;
- b) reacting said amine group of said solid support-bound linker with said carbonyl compound and said reducing agent, said reaction occurring in the presence of said aqueous solvent system and yielding an N-alkylated solid support-bound linker;
- and
- c) treating said N-alkylated solid support-bound linker, thereby generating said N-substituted amide product.
2 more elements
Dependencies are inferred from the claim text.