Heterocycles—cyclic compounds containing at least one non-carbon heteroatom (e.g., N, O, S)—are fundamental in medicinal chemistry due to their influence on a drug’s physicochemical and biological properties. They improve solubility, bioavailability, and facilitate molecular recognition through their electronic and hydrogen-bonding features. These properties make them indispensable in drug design. This study focuses on the synthesis of a key heterocyclic intermediate: benzyl-N-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]carbamate. This molecule incorporates a thiazole ring, known for its rigidity and electronic properties, that enhances target interactions. The 2-position bears a Cbz-protected amine, enabling orthogonal deprotection, while the 4-position features a hydroxyethyl side chain, providing a handle for further chemical modifications via nucleophilic substitution. Herein, we report the successful synthesis of this intermediate along with its full1H and13C NMR spectra, melting point, and crystal structure, confirming its identity and purity.

Benzyl-N-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]carbamate / L. Spinelli, M. Mori, L. Fumagalli. - In: MOLBANK. - ISSN 1422-8599. - 2025:3(2025 Jul 21), pp. M2040.1-M2040.7. [10.3390/m2040]

Benzyl-N-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]carbamate

L. Spinelli
Primo
;
M. Mori
Penultimo
;
L. Fumagalli
Ultimo
2025

Abstract

Heterocycles—cyclic compounds containing at least one non-carbon heteroatom (e.g., N, O, S)—are fundamental in medicinal chemistry due to their influence on a drug’s physicochemical and biological properties. They improve solubility, bioavailability, and facilitate molecular recognition through their electronic and hydrogen-bonding features. These properties make them indispensable in drug design. This study focuses on the synthesis of a key heterocyclic intermediate: benzyl-N-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]carbamate. This molecule incorporates a thiazole ring, known for its rigidity and electronic properties, that enhances target interactions. The 2-position bears a Cbz-protected amine, enabling orthogonal deprotection, while the 4-position features a hydroxyethyl side chain, providing a handle for further chemical modifications via nucleophilic substitution. Herein, we report the successful synthesis of this intermediate along with its full1H and13C NMR spectra, melting point, and crystal structure, confirming its identity and purity.
2-amino-thiazol-4-yl-ethyl; NMR-spectroscopy; thiazole; X-ray crystallography;
Settore CHEM-07/A - Chimica farmaceutica
21-lug-2025
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/1200215
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