N-Pivaloyl 7-aminodesacetoxycephalosporanic acid

Base Information

• Chemical Name: N-Pivaloyl 7-aminodesacetoxycephalosporanic acid
• CAS No.: 146794-70-9
• Molecular Formula: C₁₃H₁₈N₂O₄S
• Molecular Weight: 298.363
• UNII: MDO0VUD5WQ
• Nikkaji Number: J1.067.749A
• Wikidata: Q27283930
• Mol file: 146794-70-9.mol

Synonyms:7-ADCA Pivalamide;146794-70-9;N-Pivaloyl 7-aminodesacetoxycephalosporanic acid;MDO0VUD5WQ;(6R,7R)-7-(2,2-dimethylpropanoylamino)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-7-[(2,2-dimethyl-1-oxopropyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;(6R,7R)-7-((2,2-Dimethylpropanoyl)amino)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((2,2-dimethyl-1-oxopropyl)amino)-3-methyl-8-oxo-, (6R,7R)-;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((2,2-dimethyl-1-oxopropyl)amino)-3-methyl-8-oxo-, (6R-trans)-;(6R,7R)-7-(2,2-DIMETHYLPROPANAMIDO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID;UNII-MDO0VUD5WQ;Cefadroxil impurity H [EP];Cefadroxil monohydrate impurity H [EP];CEFRADINE IMPURITY G [EP IMPURITY];CEFADROXIL IMPURITY H [EP IMPURITY];A899269;J-008264;CEFADROXIL MONOHYDRATE IMPURITY H [EP IMPURITY];Q27283930

Chemical Property of N-Pivaloyl 7-aminodesacetoxycephalosporanic acid

Chemical Property:

• Boiling Point: 617.1±55.0 °C(Predicted)
• PKA: 3.13±0.50(Predicted)
• PSA: 112.01000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 1.11980
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Water (Slightly, Heated)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 298.09872823
• Heavy Atom Count: 20
• Complexity: 521

Purity/Quality:

97% ^*data from raw suppliers

7-ADCAPivalamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N2C(C(C2=O)NC(=O)C(C)(C)C)SC1)C(=O)O
• Isomeric SMILES: CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)C(C)(C)C)SC1)C(=O)O
• Uses: 7-ADCA Pivalamide is an impurity of the semi-synthetic antibiotic Cephalexin (C256800) as well as its hydroxy analogue Cefadroxil (C235750).

Technology Process of N-Pivaloyl 7-aminodesacetoxycephalosporanic acid

There total 2 articles about N-Pivaloyl 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:

C13H18N2O4S*C5H13N3 → (6R,7R)-7-[(2,2-dimethyl-1-oxopropyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (146794-70-9)

Guidance literature:

With hydrogenchloride; In water; at 25 ℃; for 0.833333h;

Reference yield:

3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) → (6R,7R)-7-[(2,2-dimethyl-1-oxopropyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (146794-70-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-dimethyl-formamide; dichloromethane / 0.83 h / 7 - 10 °C

2: 2 h / 9 - 10 °C

3: hydrogenchloride / water / 0.83 h / 25 °C

With hydrogenchloride; In dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

3-deacetyloxy-7-aminocephalosporanic acid