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

CAS

113479-65-5

Catalog Number

ACM113479655

Category

Main Products

Molecular Weight

405.30

Molecular Formula

C₁₆H₁₈Cl₂N₂O₄S

MSDS COA Spec Sheet

If you have any other questions or need other size, please get a quote.

Specification

Synonyms

7-Amino-3 chloromethyl-3-cephem-4-carboxylic Acid p-Methoxybenzyl Ester Hydrochloride; p-methoxybenzyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride;

IUPAC Name

(4-methoxyphenyl)methyl(6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride

Canonical SMILES

COC1=CC=C(C=C1)COC(=O)C2=C(CSC3N2C(=O)C3N)CCl.Cl

InChI Key

LYIIGHOYDRRHAJ-XRZFDKQNSA-N

Boiling Point

601.1ºC at 760 mmHg

Melting Point

155-157ºC

Flash Point

317.4ºC

Appearance

White powder

EC Number

601-254-0

Exact Mass

404.03600

ACLE·HCl Used in the Synthesis of Novel Fluorescent Cephalosporins

ACLE Hydrochloride for the Synthesis of Fluorescent Cephalosporins.

Xiao, Jian-Min, et al. European Journal of Medicinal Chemistry, 2013, 59, 150-159.

7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (ACLE) was selected as a scaffold to connect photosensitizer (PS), and two new fluorescent cephalosporins (TCA and TBCA) were successfully synthesized. Resluts have shown that these fluorescent cephalosporins exhibit photoinactivating activity against specific strains and fluorescence imaging capabilities.
Synthesis of fluorescent cephalosporins
· To a suspension of ACLE hydrochloride (1.0 g, 2.46 mmol) in dichloromethane (15 mL) on an ice bath was added potassium trimethylsilanolate (0.63 g, 4.94 mmol) in 10 mL acetonitrile, and 2- thienylacetyl chloride (0.304 mL, 2.46 mmol) in 8 mL dichloromethane. The resulting mixture was stirred at room temperature (rt) for 1 h, and the solvent was evaporated under reduced pressure. The resulting residue was washed, dried, filtered, evaporated and recrystallized to obtain compound 4 [p-methoxybenzyl (6R,7R)-3-chloromethyl-7b-(2-thienylacetamido)-3-cephem-4-carboxylate].
· The modification of compound 4 with amino thiophenol resulted in the formation of compound 5. Coumarin-3-carboxylic acid (3a) and benzocoumarin-3-carboxylic acid (3b) were then attached to the primary amino group of the modified ACLE to produce compound 6. After deprotecting with phenol, the desired compounds, TCA and TBCA, were obtained.

Ultrasound-assisted Synthesis of t-Butoxycarbonylamino Cephalosporin Intermediate by ACLE·HCl

Ultrasonic synthesis of Boc-ACLE with ACLE·HCl.

Xue, Feng, et al. Journal of Chemistry, 2016, 9734108.

An effective strategy for the synthesis of 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylate via ultrasonic irradiation using SiO2 as a weak Lewis acid catalyst was developed. Among them, 4-methoxybenzyl 7β-amino-3-chloromethyl-3-cephem-carboxylate (ACLE·HCl) was used to prepare 4-methoxybenzyl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-carboxylate (Boc-ACLE), achieving effective protection of N-tert-butoxycarbonyl (N-Boc).
Synthetic Procedure of t-Butoxycarbonylamino Cephalosporin Intermediates
· Starting with ACLE·HCl in CH2Cl2 (200 mL), triethylamine was added to adjust the pH to 7-8 at 0-5°C.
· SiO2 and Boc2O were then added to the mixture and ultrasonicated at 0-5°C for a specific time. Once the reaction was complete, as shown by TLC, the mixture was poured into water.
· The organic phase was separated, washed with brine water, and dried with anhydrous sodium sulfate under vacuum. The crude product was then purified using column chromatography over silica gel to obtain the desired compounds.

August 03, 2023

A pharmaceutical intermediate
7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester,hcl can be used as an intermediate of cefazolin to synthesize antibacterial agents.

What kind of compound is 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester?

7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester is an antibiotic intermediate of cephalosporins, which can be used to synthesize cefazolin.

What is the melting point of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester?

The melting point of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester is 155-157 ℃.

In what solvent does 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester have good solubility?

7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester is insoluble in water, slightly soluble in ethanol and soluble in chloroform and toluene.

What are the security risks of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester?

7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester has certain toxicity, which may cause harm if inhaled, contacted with skin or taken by mistake.

What cephalosporin antibiotics can 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester be used to synthesize?

7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester can be used to synthesize cephalosporin antibiotics such as cefazolin, cefpirin and cefepime.

What is the molecular formula of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester?

The molecular formula of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester is C16H18Cl2N2O4S.

What is the molecular weight of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester?

The molecular weight of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester is 405.29 g/mol.

What are the precautions of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester?

When using 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester, you should wear appropriate protective equipment to avoid direct contact and store it in a dry and ventilated place.

What is the usage of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester?

The dosage of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester can be adjusted according to the reaction conditions and the required yield, and is generally 0.1-1 mmol/g.

what are the storage requirements of 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester?

The storage temperature of 7-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester should be controlled between 0-10℃ to avoid too high or too low temperature affecting its stability.