2-(2-Aminothiazol-4-yl) acetic acid hydrochloride

China [CN]

Physical Properties

Appearance: Typically a white to off-white crystalline powder.

Solubility: More soluble in water than the free base form; soluble in polar solvents such as water and methanol, but has low solubility in non-polar organic solvents (e.g., petroleum ether, n-hexane).

Main Uses: As an important pharmaceutical intermediate, the amino and carboxyl groups in its structure are active reaction sites, mainly used in the synthesis of:

β-Lactam antibiotics: For example, some cephalosporin drugs, where the thiazole ring structure is a key group for enhancing antibacterial activity.

Bioactive heterocyclic derivatives: Can be used in the development of lead compounds for anti-inflammatory and antiviral drugs.

Synthesis and Reaction Characteristics

Common Synthesis Route: Using 2-aminothiazole-4-formaldehyde or halogenated 2-aminothiazole as raw materials, the acetic acid side chain is introduced through nucleophilic substitution, oxidation, or hydrolysis reactions, and finally purified by salt formation with hydrochloric acid.

Reactivity: The carboxyl group in the molecule can undergo esterification and amidation reactions; the amino group can undergo acylation and diazotization reactions, facilitating further structural modification.