Preparation of new mono- and bis-amide derivatives of L-isoleucine via amidation of carboxyl and amino groups

Original Article

JOURNAL 2139

Organic Communications

VOLUME & ISSUE

Year: 2021 Issue: 3 July-September

PAGES

p.294 - 299

DOI ADDRESS

http://doi.org/10.25135/acg.oc.112.21.07.2139

STATISTICS

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AUTHORS

Murat Sunkur
Sara Aydın
Tarık Aral
Besir Dağ
Ramazan Erenler

GRAPHICAL ABSTRACT

ABSTRACT

N,N′-Dicyclohexylcarbodiimide and hydroxybenzotriazole mediated amination of free COOH group of N-tert-butyloxyoxycarbonyl-L-isoleucine 1 with three aromatic amines gave the corresponding amides 2a-c. Deprotection of N-tert- butyloxyoxycarbonyl groups of 2a-c with AcOH yielded the related amine derivatives 3a-c. The amidation of the free NH2 groups of (3a-c) with phthaloyl dichloride yielded the bis-amide products 4a-c. The synthesized compounds were purified by crystallization and their structures were elucidated by spectroscopic methods such as 1H-HMR, 13C-NMR, FTIR, and micro analysis.

KEYWORDS

Amides
tetraamides
N-boc-deprotection
coupling reaction
spectroscopy
heterocyclic

SUPPORTING INFORMATION

Supporting Information

Download File A7-112-OC-2107-2139-SI.pdf (2.67 MB)