7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester hydrochloride

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Cat Number

INT113479655

CAS Number

113479-65-5

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Product Detail Description Customer Q&A

CAS Number

113479-65-5

EINECS

601-254-0

Storage

Store at -20℃

Synonyms

(6R,7R)-4-Methoxybenzyl7-aMino-3-(chloroMethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylatehydrochloride;7-AMino-3-chloroMethyl-3-cepheM-4-carboxylicacidp-Methoxybenzylester,HCl;7-Amino-3-chloromethyl-3-cephem-4-carboxylicacidp-methoxybenzylest;4-methoxybenzyl(6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-Chemicalbookazabicyclo[4.2.0]oct-2-ene-2-carboxylatehydrochloride;(4-methoxyphenyl)methyl(6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylatehydrochloride

Molecular Formula

C16H18Cl2N2O4S

Molecular Weight

405.29

Smiles

COC1=CC=C(C=C1)COC(=O)C2=C(CS[C@H]3N2C(=O)[C@H]3N)CCl.Cl

Appearance

Pale yellow powder

Melting Point

155-157℃

General Description

7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester Hydrochloride is a fully protected cephalosporin intermediate featuring a free 7-amino group on the beta-lactam ring, a chloromethyl substituent at the C-3 position of the cephem nucleus, a carboxylic acid protected as the p-methoxybenzyl ester at C-4, and formulated as the hydrochloride salt. This compound is a key advanced intermediate in the synthesis of semisynthetic cephalosporin antibiotics.

Mechanism of Action

7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester Hydrochloride functions as a beta-lactam antibiotic intermediate. The 7-amino group is the site of acylation with various side-chain acids (D-phenylglycine derivatives, aminothiazole-oxime derivatives) to generate diverse semisynthetic cephalosporins with improved spectrum and pharmacokinetics. The 3-chloromethyl group is a leaving group that can be displaced by pyridines, tetrazoles, or other heterocyclic nucleophiles to modify the C-3 side chain.

Application

7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester Hydrochloride is used as a key intermediate in the synthesis of semisynthetic cephalosporin antibiotics including cefotaxime, ceftriaxone, and related third-generation cephalosporins. The p-methoxybenzyl ester protecting group is removed by hydrogenolysis after C-7 side-chain attachment, and the resulting carboxylic acid is converted to salts or other formulations. The chloromethyl group enables C-3 side-chain modification via nucleophilic displacement.

What is the recommended storage condition for 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester hydrochloride?

It should be stored at -20°C in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester hydrochloride?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

Is 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester hydrochloride available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

What is the primary synthetic application of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester hydrochloride?

It is widely used as a key building block or intermediate in multi-step pharmaceutical synthesis workflows, providing versatile reactivity for constructing target molecular architectures.

Is 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester hydrochloride manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.