7 β - aMino - 3 - [4 - pyridyl - 2 - thiazole sulfur radical ] - 3 - cepheM - 4 - carboxylic acid

Base Information

• Chemical Name: 7 β - aMino - 3 - [4 - pyridyl - 2 - thiazole sulfur radical ] - 3 - cepheM - 4 - carboxylic acid
• CAS No.: 189345-52-6
• Molecular Formula: C16H14N4O3S3
• Molecular Weight: 406.49
• Mol file: 189345-52-6.mol

Synonyms:7 β - aMino - 3 - [4 - pyridyl - 2 - thiazole sulfur radical ] - 3 - cepheM - 4 - carboxylic acid

Chemical Property of 7 β - aMino - 3 - [4 - pyridyl - 2 - thiazole sulfur radical ] - 3 - cepheM - 4 - carboxylic acid

Chemical Property:

• PSA: 182.07000
• LogP: 0.56880

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7 β - aMino - 3 - [4 - pyridyl - 2 - thiazole sulfur radical ] - 3 - cepheM - 4 - carboxylic acid

There total 10 articles about 7 β - aMino - 3 - [4 - pyridyl - 2 - thiazole sulfur radical ] - 3 - cepheM - 4 - carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

C24H20N4O4S3 → 7β-amino-3-[4-(1-methyl-4-pyridinio)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate (189345-52-6)

Guidance literature:

With sodium hydrogencarbonate; at 30 - 37 ℃; pH=7.8 - 8.5; pH-value; Concentration; Reagent/catalyst; Enzymatic reaction;

Reference yield:

4-{2-[(6R,7R)-7-Amino-2-(4-methoxy-benzyloxycarbonyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylsulfanyl]-thiazol-4-yl}-1-methyl-pyridinium; chloride → 7β-amino-3-[4-(1-methyl-4-pyridinio)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate (189345-52-6)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(03)00126-3

Reference yield:

(7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester (123054-30-8) → 7β-amino-3-[4-(1-methyl-4-pyridinio)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate (189345-52-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C

2.1: dimethylformamide / 16 h / 20 °C

3.1: phosphorus pentachloride; pyridine / CH₂Cl₂ / 1 h / 5 °C

3.2: MeOH / CH₂Cl₂ / 0.5 h / -20 °C

4.1: 8.28 g / TFA; anisole / CH₂Cl₂ / 1 h / 20 °C

With pyridine; phosphorus pentachloride; sodium hydride; methoxybenzene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00126-3

upstream raw materials:

(7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester

[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

p-methoxybenzyl 7β-phenylacetamido-3-[4-(4-pyridyl)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate

(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Downstream raw materials:

ceftaroline