7-Aminodesacetoxycephalosporanic acid

Base Information

• Chemical Name: 7-Aminodesacetoxycephalosporanic acid
• CAS No.: 26395-99-3
• Molecular Formula: C8H10N2O3S
• Molecular Weight: 214.245
• Hs Code.: 2934999090
• European Community (EC) Number: 244-870-1
• UNII: ANM3MSM8TN
• DSSTox Substance ID: DTXSID4057687
• Nikkaji Number: J94.619B
• Wikidata: Q27133562
• Metabolomics Workbench ID: 63605
• ChEMBL ID: CHEMBL3182744
• Mol file: 26395-99-3.mol

Synonyms:7-ADCA;7-aminodeacetoxycephalosporanic acid;7-aminodesacetoxycephalosporanic acid;7-desacetoxyaminocephalosporanic acid

Chemical Property of 7-Aminodesacetoxycephalosporanic acid

Chemical Property:

• Vapor Pressure: 4.18E-12mmHg at 25°C
• Refractive Index: 1.697
• Boiling Point: 517.598 °C at 760 mmHg
• PKA: 3.04±0.50(Predicted)
• Flash Point: 266.834 °C
• PSA: 108.93000
• Density: 1.598 g/cm³
• LogP: 0.22560
• Storage Temp.: -20°C Freezer
• Solubility.: Aqueous Base (Slightly), DMSO (Very Slightly, Heated)
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 214.04121336
• Heavy Atom Count: 14
• Complexity: 353

Purity/Quality:

99% ^*data from raw suppliers

7-Aminodesacetoxycephalosporanic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N2C(C(C2=O)N)SC1)C(=O)O
• Isomeric SMILES: CC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O
• Uses: 7-Aminodesacetoxycephalosporanic Acid (Cefadroxil EP Impurity B) is a metabolite of Cephalexin (C256800).

Technology Process of 7-Aminodesacetoxycephalosporanic acid

There total 34 articles about 7-Aminodesacetoxycephalosporanic acid 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: 100.0%

(6R,7R)-7-Amino-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-methyl-but-2-enyl ester → 3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9)

Guidance literature:

With diethylamine; Pd⁽⁰⁾ (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine); In water; acetonitrile; for 1h; 5 molpercent catalyst;

DOI:10.1016/S0040-4039(00)78497-8

Reference yield: 48.0%

→ 3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) + pyridine-4-carboxylic acid (55-22-1)

Guidance literature:

Reference yield:

7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid (30246-33-4) → 7-amino-3-methylenecepham-4-carboxylic acid (36996-01-7,51795-31-4) + 7-aminodesacetoxycephalosporanic acid (26395-99-3)

Guidance literature:

With N,N-Bis(trimethylsilyl)urea; ammonium chloride; zinc; In N,N-dimethyl-formamide; 1.) 25 deg C, 13 min, 2.) 5 deg C, 18 min, 3.) 5 deg C, 30 min;

DOI:10.1248/cpb.36.582

upstream raw materials:

7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

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

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

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

Downstream raw materials:

(6R)-7t-amino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Deacetoxy-7-(D-α-1'-Cyclohexenylglycinamido)-cephalosporansaeure

(6R)-7t-[(Ξ)-2-acetoxy-2-(4-chloro-phenyl)-acetylamino]-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R)-7t-[(Ξ)-2-acetoxy-2-(4-bromo-phenyl)-acetylamino]-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Refernces

• 1、 -. "PROCESS FOR THE PRODUCTION OF CEPHALOSPORINS". Page/Page column 10-11. . Retrieved 2012/03/27.
• 2、 Blum, Janna K.,Bommarius, Andreas S.. "Amino ester hydrolase from Xanthomonas campestris pv. campestris, ATCC 33913 for enzymatic synthesis of ampicillin". scheme or table. p. 21 - 28. Retrieved 2010/12/19.