1-(4,5-Dihydrothiazol-2-yl)azetidine-3-thiol hydrochloride

The tebipenem side-chain intermediate is 1-(4,5-dihydrothiazol-2-yl)azetidine-3-thiol hydrochloride. It supplies the preassembled azetidine–thiazoline fragment and a reactive thiol for attachment to an activated carbapenem core. Sulfur coupling creates the thioether linkage found in tebipenem, while the nitrogen-containing rings transfer the required side-chain architecture into the antibiotic framework.

The selected material is the isolated hydrochloride with an unprotected thiol, rather than tebipenem itself or the pivoxil prodrug. This distinction places it at the side-chain coupling stage of synthesis. The salt and sulfur functionality determine how the reagent is introduced into the coupling sequence, and the completed carbapenem structure still requires the appropriate protection, deprotection or prodrug operations of the chosen route.

Typical Applications

• Tebipenem side-chain installation: Used as the sulfur nucleophile in coupling with a suitably activated carbapenem intermediate, forming the carbon–sulfur bond that joins the azetidine–thiazoline fragment to the beta-lactam framework.
• Tebipenem pivoxil process development: Used in routes to the oral prodrug as the defined side-chain feedstock, enabling study of coupling conversion and side-chain-related by-products before downstream prodrug isolation.

Specifications

Specifications describe the standard grade. Tolerance, test method and documentation package are confirmed per order.