5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-ethenyl-8-oxo-7-[(phenylacetyl)amino]-, (6R,7R)-

Base Information

• Chemical Name: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-ethenyl-8-oxo-7-[(phenylacetyl)amino]-, (6R,7R)-
• CAS No.: 33748-00-4
• Molecular Formula: C17H16N2O4S
• Molecular Weight: 344.391
• Mol file: 33748-00-4.mol

Synonyms:

Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-ethenyl-8-oxo-7-[(phenylacetyl)amino]-, (6R,7R)-

Chemical Property:

• Boiling Point: 726.1±60.0 °C(Predicted)
• PSA: 112.01000
• Density: 1.44±0.1 g/cm3(Predicted)
• LogP: 1.48250

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Cefixime Impurity can be used in the impurity reference and standard etc.

Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-ethenyl-8-oxo-7-[(phenylacetyl)amino]-, (6R,7R)-

There total 6 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-ethenyl-8-oxo-7-[(phenylacetyl)amino]-, (6R,7R)- 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: 96.0%

diphenylmethyl 7β-phenylacetamido-3-vinyl-3-cephem-4-carboxylate (94796-13-1) → 7-(phenylacetamido)-3-vinylcephem-4-carboxylic acid (33748-00-4)

Guidance literature:

In methanol; for 1h; Reflux;

Reference yield:

7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester (119608-90-1) → 7-(phenylacetamido)-3-vinylcephem-4-carboxylic acid (33748-00-4)

Guidance literature:

With phenol; at 45 - 50 ℃; Large scale reaction; neat (no solvent);

DOI:10.1021/op900053j

Reference yield:

(6R,7R)-benzhydryl 3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (64308-63-0) → 7-(phenylacetamido)-3-vinylcephem-4-carboxylic acid (33748-00-4)

Guidance literature:

Multi-step reaction with 3 steps

1: nitric acid; sodium bromide / acetone / 3 h / 40 °C

2: potassium carbonate; sodium hydroxide / 2 h / 0 - 10 °C

3: methanol / 1 h / Reflux

With nitric acid; potassium carbonate; sodium bromide; sodium hydroxide; In methanol; acetone;

upstream raw materials:

7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester

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

diphenylmethyl 7β-phenylacetamido-3-vinyl-3-cephem-4-carboxylate

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Downstream raw materials:

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Refernces

• 1、 -. "A method for synthesizing spore parent nucleus antibiotiki head". . . Retrieved 2017/01/02.