Desacetyl-cephalosporanic acid | Pharmaceutical Grade | 99.99% Purity | 10mg 20mg 30mg Vials | Lyophilized Powder | CAS 15690-38-7

Desacetyl-cephalosporanic acid

Chemical Properties
The amino group in the molecular structure can undergo condensation reactions with acid chlorides under alkaline conditions to generate corresponding amide derivatives.
Chemical Reactions
7-Aminocephalosporanic acid can react with ammonium (Z)-2-furyl-2-methoxyiminoacetate and phosphorus pentachloride in alkaline aqueous solution via condensation to produce (6R,7R)-7-[(Z)-2-(2-furyl)-2-methoxyiminoacetamido]-3-hydroxymethyl-3-cephem-4-carboxylic acid.
Applications
It serves as a key pharmaceutical intermediate and the core mother nucleus widely used for cephalosporin antibiotics. 7-ACA contains two active functional groups: the 3-position acetoxy group and the 7-position amino group. Different side chains attached to these two active sites can form cephalosporin antibiotics with distinct properties, including cefotaxime, ceftriaxone, cefazolin, cefuroxime, cefoperazone and others.
Production Process
CAS No. 957-68-6
CAS No. 15690-38-7
General synthetic procedure for (6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid starting from 7-aminocephalosporanic acid (7-ACA):
Accurately weigh 27.2 g (0.1 mol) of 7-ACA and transfer it into a reaction flask, then add a mixed solvent containing 50 mL methanol and 50 mL water. Maintain the temperature between -5 °C and 5 °C, add 3.0 g tetra-n-butylammonium chloride under continuous stirring, followed by slow dropwise addition of 2 mol/L sodium hydroxide aqueous solution. After dripping is completed, keep the reaction temperature and stir the mixture for another 0.5 to 1 hour. Upon reaction completion, adjust the pH value of the reaction mixture to neutral using 30% hydrochloric acid, during which solid precipitates are generated. Collect solid products via suction filtration and rinse with anhydrous ethanol. 20.7 g of dried white solid product is obtained finally. High performance liquid chromatography (HPLC, area normalization method) analysis shows the product purity reaches 97.35%, with lactone impurity content of 0.33%.
References
[1] Patent CN105131017, 2017, B. Paragraph 0041-0042
[2] Synthetic Communications, 2003, Volume 33, Issue 14, Pages 2475-2482
[3] Patent CN106083894, 2016, A. Paragraph 0045; 0054; 0055; 0056; 0057
[4] Synthesis, 2012, Volume 2012, Issue 2, Pages 207-214
[5] Farmaco, 2003, Volume 58, Issue 6, Pages 409-418