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| | Hydroxymethyl-7-Aminocephalosporanic acid Basic information |
| Product Name: | Hydroxymethyl-7-Aminocephalosporanic acid | | Synonyms: | 7-ACA Impurity 1（Deacetyl 7-ACA）;Ceftriaxone Impurity 22;Cephalosporin impurity 1;7-ACA Impurity D;Cefazedone Impurity 11;(2S)-N-[(2S,4R)-4-acetamido-1-[[(2S)-2-[[(2R)-6-amino-2-[[(2S)-3-(4-hydroxyphenyl)-2-(methylamino)-1-oxopropyl]amino]-1-oxohexyl]amino]-4-methyl-1-oxopentyl]-[(2S)-2-[[(2R)-2-amino-1-oxo-3-(3-pyridiny;7-Amino-3-(hydroxymethyl)-cephem-4-carboxylic acid;Intermediate of cefoselis Sulfate (7-Amino-3-(hydroxymethyl)-3-cephem-4-carboxylic acid ) | | CAS: | 15690-38-7 | | MF: | C8H10N2O4S | | MW: | 230.24 | | EINECS: | 239-787-2 | | Product Categories: | Cefcapene;15690-38-7 | | Mol File: | 15690-38-7.mol |  |
| | Hydroxymethyl-7-Aminocephalosporanic acid Chemical Properties |
| Melting point | 105-107°C | | Boiling point | 617.9±55.0 °C(Predicted) | | density | 1.74 | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 2.68±0.50(Predicted) | | form | Solid | | color | White to Beige | | InChI | InChI=1S/C8H10N2O4S/c9-4-6(12)10-5(8(13)14)3(1-11)2-15-7(4)10/h4,7,11H,1-2,9H2,(H,13,14)/t4-,7-/m1/s1 | | InChIKey | BQIMPGFMMOZASS-CLZZGJSISA-N | | SMILES | N12[C@@]([H])([C@H](N)C1=O)SCC(CO)=C2C(O)=O |
| | Hydroxymethyl-7-Aminocephalosporanic acid Usage And Synthesis |
| Chemical Properties | Beige Solid | | Uses | Intermediate in the semi-synthetic cephalosporins synthesis. Found in Acremonium chrysogenum. | | Synthesis | General procedure for the synthesis of (6R,7R)-7-amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid from 7-aminocephalosporanic acid (7-ACA): 27.2 g (0.1 mol) of 7-ACA were accurately weighed and placed in a reaction flask, to which 50 mL of methanol and 50 mL of water were added as solvents. 3.0 g of tetra-n-butyl ammonium chloride was added while stirring at a temperature of -5 to 5 °C. Subsequently, 2 mol/L sodium hydroxide solution was added slowly dropwise. After the dropwise addition was completed, the reaction temperature was maintained and stirring was continued for 0.5 to 1 hour. Upon completion of the reaction, the pH of the reaction solution was adjusted to neutral with 30% hydrochloric acid, at which point a solid precipitated. The solid product was collected by diafiltration and washed with anhydrous ethanol. Eventually, 20.7 g of dry white solid product was obtained. The product was analyzed by high performance liquid chromatography (HPLC) and the purity of the product was 97.35% (area normalization method) and the content of lactone impurities was 0.33%. | | References | [1] Patent: CN105131017, 2017, B. Location in patent: Paragraph 0041-0042
[2] Synthetic Communications, 2003, vol. 33, # 14, p. 2475 - 2482
[3] Patent: CN106083894, 2016, A. Location in patent: Paragraph 0045; 0054; 0055; 0056; 0057
[4] Synthesis, 2012, vol. 2012, # 2, p. 207 - 214
[5] Farmaco, 2003, vol. 58, # 6, p. 409 - 418 |
| | Hydroxymethyl-7-Aminocephalosporanic acid Preparation Products And Raw materials |
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