Synthesis of heterobifunctional crosslinking reagents

ω-(N-Maleimido)-alkanoic acid hydrazides

Sarvottam Y. Ambekar, Channe Gowda

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

ω-(N-Maleimido)alkanoic acid hydrazides (6a-c) with C11, C7 and C5 alkyl arms have been synthesized by novel method. The method involves the reaction between maleic anhydride and ω-aminoalkanoic acids (2) to get maleamic acids (3) which are in turn cyclized to ω-(N̄-maleimido)alkanoic acids (4) using fused sodium acetate and acetic anhydride. These maleimidoalkanoic acids are activated and then converted in situ into their N-2-t-butyloxycarbonyl hydrazides (5) from which the t-butyl-based protecting group is cleaved without damage to the maleimide molety to obtain the title compounds.

Original languageEnglish (US)
Pages (from-to)184-186
Number of pages3
JournalIndian Journal of Chemistry - Section B Organic and Medicinal Chemistry
Volume35
Issue number3
StatePublished - Mar 1996

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Cross-Linking Reagents
Carboxylic acids
Maleic Anhydrides
Sodium Acetate
Acids
maleamic acid
maleimide
acetic anhydride

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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title = "Synthesis of heterobifunctional crosslinking reagents: ω-(N-Maleimido)-alkanoic acid hydrazides",
abstract = "ω-(N-Maleimido)alkanoic acid hydrazides (6a-c) with C11, C7 and C5 alkyl arms have been synthesized by novel method. The method involves the reaction between maleic anhydride and ω-aminoalkanoic acids (2) to get maleamic acids (3) which are in turn cyclized to ω-(N̄-maleimido)alkanoic acids (4) using fused sodium acetate and acetic anhydride. These maleimidoalkanoic acids are activated and then converted in situ into their N-2-t-butyloxycarbonyl hydrazides (5) from which the t-butyl-based protecting group is cleaved without damage to the maleimide molety to obtain the title compounds.",
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T2 - ω-(N-Maleimido)-alkanoic acid hydrazides

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AU - Gowda, Channe

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N2 - ω-(N-Maleimido)alkanoic acid hydrazides (6a-c) with C11, C7 and C5 alkyl arms have been synthesized by novel method. The method involves the reaction between maleic anhydride and ω-aminoalkanoic acids (2) to get maleamic acids (3) which are in turn cyclized to ω-(N̄-maleimido)alkanoic acids (4) using fused sodium acetate and acetic anhydride. These maleimidoalkanoic acids are activated and then converted in situ into their N-2-t-butyloxycarbonyl hydrazides (5) from which the t-butyl-based protecting group is cleaved without damage to the maleimide molety to obtain the title compounds.

AB - ω-(N-Maleimido)alkanoic acid hydrazides (6a-c) with C11, C7 and C5 alkyl arms have been synthesized by novel method. The method involves the reaction between maleic anhydride and ω-aminoalkanoic acids (2) to get maleamic acids (3) which are in turn cyclized to ω-(N̄-maleimido)alkanoic acids (4) using fused sodium acetate and acetic anhydride. These maleimidoalkanoic acids are activated and then converted in situ into their N-2-t-butyloxycarbonyl hydrazides (5) from which the t-butyl-based protecting group is cleaved without damage to the maleimide molety to obtain the title compounds.

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