(6R)-3-(acetoxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: (6R)-3-(acetoxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 957-68-6
• Molecular Formula: C10H12N2O5S
• Molecular Weight: 272.282
• Hs Code.: 2934.90
• Mol file: 957-68-6.mol

Synonyms:(6R)-3-(acetoxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;(7R)-7 aminocephalosporanate;SCHEMBL10364275;CHEBI:58501;7beta-aminocephalosporanic acid zwitterion;A845463;(6R,7R)-3-(acetyloxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;(6R,7R)-3-(acetyloxymethyl)-7-azaniumyl-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property of (6R)-3-(acetoxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

• Appearance/Colour: off-white to beige crystalline powder
• Vapor Pressure: 4.87E-14mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.66
• Boiling Point: 560.6 °C at 760 mmHg
• PKA: 2.59±0.50(Predicted)
• Flash Point: 292.9 °C
• PSA: 135.23000
• Density: 1.6 g/cm³
• LogP: -0.23120
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Very Slightly, Heated)
• Water Solubility.: 409.6mg/L(22.99 oC)
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 272.04669266
• Heavy Atom Count: 18
• Complexity: 456

Purity/Quality:

99% ^*data from raw suppliers

7-Aminocephalosporanic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xn,Xi
• Statements: 42/43-36/37/38-20/21/22
• Safety Statements: 22-36/37-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)[NH3+])SC1)C(=O)[O-]
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)[NH3+])SC1)C(=O)[O-]
• Uses: Pharmaceutical intermediates. It is the starting material of many semi-synthetic cephalosporin. A variety of semi-synthetic cephalosporin industrial production is through fermentation to obtain cephalosporin C. Then obtain nucleus 7-ACA through chemical cleavage , and then the preparation is fininshed in chemically modified way . It is the starting material for semi-synthetic cephalosporins. Obtained by mild acid hydrolysis of cephalosporin C. Potent inhibitor of bacterial (S. aureus) β-lactamase. 7-Aminocephalosporanic Acid (Cefoperazone EP Impurity E) is the starting material for semi-synthetic cephalosporins. Obtained by mild acid hydrolysis of cephalosporin C.
• production method: Starting from the basic raw material of semi-synthetic cephalosporin-cephalosporin C, after esterification with trimethylchlorosilane , and then by phosphorus pentachloride chloride, and Butanol etherifying, and the production is obtained finally through hydrolysis. Yield from cephalosporin C sodium to 7-ACA is about 50%.

Technology Process of (6R)-3-(acetoxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 16 articles about (6R)-3-(acetoxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 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%

cephalosporin C (61-24-5) → 7-Aminocephalosporanic acid (957-68-6)

Guidance literature:

With phosphate buffer; enzyme derivative DAO; enzyme derivative GA; at 25 ℃; for 2h; pH 8;

DOI:10.1021/jo971166u

Reference yield: 91.2%

→ 7-Aminocephalosporanic acid (957-68-6)

Guidance literature:

Reference yield: 84.0%

benzhydryl 7-aminocephalosporanate (27266-61-1,54600-89-4) → 7-Aminocephalosporanic acid (957-68-6)

Guidance literature:

With formic acid; at 40 - 45 ℃; for 0.5h; Product distribution;

DOI:10.1248/cpb.30.4545

upstream raw materials:

benzhydryl 7-aminocephalosporanate

acetic acid

cephalosporin C

3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid

Downstream raw materials:

(6R)-3-acetoxymethyl-8-oxo-7t-(2-phenylsulfanyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester

7-amino-3-<(3,4-dihydoxyphenyl)methyl>ceph-3-em-4-carboxylic acid

<6R<6α,7β(Z)>>-3-(acetoxymethyl)-7-<(methoxyimino)<2-(triphenylmethyl)amino-4-thiazolyl>acetylamino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid (1:1) triethylamine salt

(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid

Refernces

• 1、 Wei, Yanmei,Luo, Hui,Chang, Yanhong,Yu, Huimin,Shen, Zhongyao. "Reversible immobilization of cephalosporin C acylase on epoxy supports coated with polyethyleneimine". . p. 250 - 259. Retrieved 2015.
• 2、 Terreni, Marco,Tchamkam, Joseph Gapesie,Sarnataro, Umberto,Rocchietti, Silvia,Fernandez-Lafuente, Roberto,Guisan, Jose M.. "Influence of substrate structure on PGA-catalyzed acylations. Evaluation of different approaches for the enzymatic synthesis of cefonicid". . p. 121 - 128. Retrieved 2007/10/03.