Deacetylcefotaxime lactone

Base Information

• Chemical Name: Deacetylcefotaxime lactone
• CAS No.: 66340-33-8
• Molecular Formula: C₁₄H₁₃N₅O₅S₂
• Molecular Weight: 395.42
• Hs Code.: 2941906000
• UNII: 3Z40JM5X8L
• DSSTox Substance ID: DTXSID70216550
• Mol file: 66340-33-8.mol

Synonyms:Deacetylcefotaxime lactone;66340-33-8;Ceftriaxone impurity B;3-Desacetyl Cefotaxime Lactone;3Z40JM5X8L;(2Z)-2-(2-amino-1,3-thiazol-4-yl)-N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.02,5]undec-1(8)-en-4-yl]-2-methoxyiminoacetamide;(5aR,6R)-6-(((2Z)-2-(2-Aminothiazol-4-yl)-2-(methoxyimino)acetyl)amino)-5a,6-dihydro-3H,7H-azeto(2,1-b)furo(3,4-d)(1,3)thiazine-1,7(4H)-dione;Cefotaxime impurity E [EP];UNII-3Z40JM5X8L;Cefotaxime sodium impurity E [EP];Ceftriaxone sodium impurity B [EP];Cefotaxime specified impurity E [EP];DTXSID70216550;AKOS030530217;4-Thiazoleacetamide, 2-amino-alpha-(methoxyimino)-N-(1,4,5a,6-tetrahydro-1,7-dioxo-3H,7H-azeto(2,1-b)furo(3,4-d)(1,3)thiazin-6-yl)-, (5ar-(5aalpha,6beta(Z)))-;CEFTRIAXONE SODIUM IMPURITY B [IP];CEFOTAXIME IMPURITY E [EP IMPURITY];HY-135394;CS-0112380;CEFOTAXIME SODIUM IMPURITY E [EP IMPURITY];CEFTRIAXONE SODIUM IMPURITY A [USP IMPURITY];CEFTRIAXONE SODIUM IMPURITY B [EP IMPURITY];4-THIAZOLEACETAMIDE, 2-AMINO-.ALPHA.-(METHOXYIMINO)-N-(1,4,5A,6-TETRAHYDRO-1,7-DIOXO-3H,7H-AZETO(2,1-B)FURO(3,4-D)(1,3)THIAZIN-6-YL)-, (5AR-(5A.ALPHA.,6.BETA.(Z)))-

Chemical Property of Deacetylcefotaxime lactone

Chemical Property:

• PKA: 8.25±0.20(Predicted)
• Density: 1.99±0.1 g/cm3(Predicted)
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 395.03581088
• Heavy Atom Count: 26
• Complexity: 741

Purity/Quality:

97% ^*data from raw suppliers

3-Desacetyl cefotaxime lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C4=C(COC4=O)CS3
• Isomeric SMILES: CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C4=C(COC4=O)CS3
• Uses: 3-Desacetyl Cefotaxime Lactone is an impurity of Cefotaxime sodium (C242950). 3-Desacetyl Cefotaxime Lactone is also a degradation product for other cephalosporin antibiotics such as: Ceftriaxone (C245000), Cefodizime and Ceftiofur (C244700).

Technology Process of Deacetylcefotaxime lactone

There total 2 articles about Deacetylcefotaxime lactone 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:

Kenicef (86329-79-5) → (-)-(6R,7R)-7-<(Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido>-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid lactone (66340-33-8) + Cefodizime (97180-26-2,120533-29-1)

Guidance literature:

With hydrogenchloride; McIlvaine buffer; In water; at 100 ℃; Mechanism; Product distribution; degradation in various conditions (reagents, temperatures, pH);

DOI:10.1248/cpb.37.367

Reference yield:

cefotaxime (758680-79-4,152186-43-1) → 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid (91868-79-0) + desacetoxycefotaxime (65052-63-3) + desacetylcefotaxime (66340-28-1,121020-94-8,74440-61-2,99124-78-4) + desacetylcefotaxime lactone (66340-33-8) + 7-aminocephalosporanic acid (108260-00-0)

Guidance literature:

With bromine; In methanol; water; at 20 ℃; Product distribution; number "n" of bromine molecules consumed by one molecule of the compound;;

DOI:10.1021/ac00153a008

upstream raw materials:

Kenicef

cefotaxime