Introduction of histidine units using benzotriazolide activation

Bajaj, Kiran; Panda, Siva S.; Ibrahim, Mohamed A.; El‐Feky, Said A.; Katritzky, Alan R.

doi:10.1002/psc.2483

Cited by 4 publications

(3 citation statements)

References 28 publications

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“…N ‐(Cbz‐ α ‐Aminoacyl)benzotriazoles 7a–g (Scheme ) were prepared in 64–88% yields from the corresponding N ‐Cbz‐ α ‐amino acids following our published procedure ().…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Antimalarial Bioassay of Quinine – Peptide Conjugates

et al. 2013

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“…N ‐(Cbz‐ α ‐Aminoacyl)benzotriazoles 7a–g (Scheme ) were prepared in 64–88% yields from the corresponding N ‐Cbz‐ α ‐amino acids following our published procedure ().…”

Section: Resultsmentioning

confidence: 99%

“…Preparation of N-Cbz-aminoacylbenzotriazoles 7a-g N-(Cbz-a-Aminoacyl)benzotriazoles 7a-g (Scheme 2) were prepared in 64-88% yields from the corresponding N-Cbza-amino acids following our published procedure (20,21).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimalarial Bioassay of Quinine – Peptide Conjugates

et al. 2013

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“…N-Protected aminoacyl benzotriazoles are stable crystalline compounds and have been extensively used in our group for various nucleophilic acyl substitution reactions under mild conditions. 23,24 Moreover, it was proved earlier that these reactions take place without racemization [23][24][25] and provide powerful tool for the amide bond construction with retention of chirality at an asymmetric carbon atom. [26][27][28] We first developed a standard procedure for the preparation of thioacids from N-acylbenzotriazoles.…”

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A Facile Synthesis of Thioacids from N-Acylbenzotriazoles

Khaybullin

Panda

Al‐Youbi

et al. 2013

Synlett

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1. General Information S2 2. Experimental Procedures and Characterization of compounds 2a-h and 4a-d S2 3. Copy of 1 H, 13 C NMR and CHN/HRMS spectra for compounds 2a-h and 4a-d S15 S2 General Information. All commercial materials (Aldrich, Fluka) were used without further purification. All solvents were reagent grade or HPLC grade (Fisher Solvents were dried using standard protocols kept under a dry atmosphere of nitrogen. Melting points were determined on a capillary point apparatus equipped with a digital thermometer and are uncorrected. 1 H NMR and 13 C NMR spectra were recorded in CDCl 3 or DMSO-d 6 or CD 3 OD using a 300 MHz spectrometer (with TMS as an internal standard) at ambient temperature unless otherwise stated. Chemical shifts are reported in parts per million relative to residual solvent CDCl 3 (1 H, 7.26 ppm; 13 C, 77.23 ppm), DMSO-d 6 (1 H, 2.50 ppm; 13 C, 39.51 ppm). All 13 C NMR spectra were recorded with complete proton decoupling. The data have been reported in order to provide the maximum amount of information regarding coupling constants, which has necessarily led to integrals reported following a group of peaks in some instances. High-resolution and highperformance liquid chromatography mass spectral analyses were performed by the University of Florida chemistry department facility staff. Reactions were carried out in oven-dried glassware under an argon or nitrogen atmosphere unless otherwise noted. Analytical TLC was performed on E. Merck silica gel 60 F254 plates and visualized by UV and potassium permanganate staining. Flash column chromatography was performed on E. Merck silica gel 60 (40-63 mm). Yields refer to chromatographically and spectroscopically pure compounds. Mass spectrometry was done with electro spray ionization (ESI). Experimental Section General procedure for the preparation of N-protected amino thioacids 2a-h and Nprotected di-and tripeptide thioacids 4a-d H 2 S was bubbled through precooled (0 o C) solution of N-protected-aminoacylbenzotriazole (1.0 mmol), NMM (1 mmol) in THF (10 mL) for 5 min. The reaction mixture was allowed to

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Preparation, Reactivity, and Synthetic Utility of Simple Benzotriazole Derivatives

Gérardy

Monbaliu

2015

Topics in Heterocyclic Chemistry

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Introduction of histidine units using benzotriazolide activation

Cited by 4 publications

References 28 publications

Synthesis and Antimalarial Bioassay of Quinine – Peptide Conjugates

Synthesis and Antimalarial Bioassay of Quinine – Peptide Conjugates

A Facile Synthesis of Thioacids from N-Acylbenzotriazoles

Preparation, Reactivity, and Synthetic Utility of Simple Benzotriazole Derivatives

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