Phenylacetyl 7-aminodesacetoxycephalosporanic acid

Base Information

• Chemical Name: Phenylacetyl 7-aminodesacetoxycephalosporanic acid
• CAS No.: 27255-72-7
• Molecular Formula: C16H16 N2 O4 S
• Molecular Weight: 332.38
• European Community (EC) Number: 248-379-3
• DSSTox Substance ID: DTXSID00181707
• Nikkaji Number: J428.379A
• Wikidata: Q72501142
• ChEMBL ID: CHEMBL115860
• Mol file: 27255-72-7.mol

Synonyms:7-(phenylacetamido)desacetoxycephalosporanic acid;PA-7-ADACA;phenylacetyl 7-aminodesacetoxycephalosporanic acid;phenylacetyl 7-aminodesacetoxycephalosporanic acid, potassium salt

Chemical Property of Phenylacetyl 7-aminodesacetoxycephalosporanic acid

Chemical Property:

• Vapor Pressure: 5.08E-21mmHg at 25°C
• Boiling Point: 707.7°C at 760 mmHg
• PKA: 3.13±0.50(Predicted)
• Flash Point: 381.8°C
• PSA: 112.01000
• Density: 1.46g/cm³
• LogP: 1.31640
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 332.08307817
• Heavy Atom Count: 23
• Complexity: 568

Purity/Quality:

97% ^*data from raw suppliers

7-PHENYL-ACETAMIDO-DEACETOXY-CEPHALOSPORANIC-ACID 95.00% ^*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)CC3=CC=CC=C3)SC1)C(=O)O
• Isomeric SMILES: CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CC3=CC=CC=C3)SC1)C(=O)O
• Use Description: 7-Phenyl-acetamido-deacetoxy-cephalosporanic acid is a chemical compound with important applications, particularly in the field of pharmaceuticals. It serves as a crucial intermediate in the synthesis of cephalosporin antibiotics, a class of antimicrobial drugs widely used in medicine. By modifying and functionalizing 7-Phenyl-acetamido-deacetoxy-cephalosporanic-acid, chemists can create various cephalosporin antibiotics, each with specific properties and applications. These antibiotics play a vital role in treating bacterial infections and are used in the healthcare industry to combat a wide range of pathogens. Additionally, they contribute to the ongoing effort to combat antibiotic-resistant bacteria. Therefore, the role of 7-Phenyl-acetamido-deacetoxy-cephalosporanic acid in pharmaceuticals is fundamental, as it facilitates the production of antibiotics that save lives and improve public health.

Technology Process of Phenylacetyl 7-aminodesacetoxycephalosporanic acid

There total 15 articles about Phenylacetyl 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: 94.0%

Penicillin G 1-(s)-oxide (4052-54-4) → 7-phenylacetamidodesacetoxycephalosporanic acid (27255-72-7)

Guidance literature:

Penicillin G 1-(s)-oxide; With N,N'-bis(trimethylsilyl)urea; In toluene; at 60 - 70 ℃; for 1h; Large scale;

With Pyridine hydrobromide; In toluene; at 70 - 80 ℃; Concentration; Large scale;

DOI:10.1021/op300076q

Reference yield: 69.4%

tert-butyl (6R,7R)-3-methyl-7-phenyl-acetamido-ceph-3-em-4-carboxylate → 7-phenylacetamidodesacetoxycephalosporanic acid (27255-72-7)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(97)10857-7

Reference yield: 54.0%

2-chloro-2-propenyl (6R,7R)-3-methyl-7-(phenylacetamido)-8-oxo-3-cephem-4-carboxylate (80127-26-0) → 7-phenylacetamidodesacetoxycephalosporanic acid (27255-72-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium 2-ethylhexanoate; triphenylphosphine; In dichloromethane; ethyl acetate; for 1h; Ambient temperature;

DOI:10.1021/jo00342a048

upstream raw materials:

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

2-chloro-2-propenyl (6R,7R)-3-methyl-7-(phenylacetamido)-8-oxo-3-cephem-4-carboxylate

cephaloram

7-(phenylacetamido)-3-exo-methylenecepham-4-carboxylic acid

Downstream raw materials:

C₁₆H₁₅O₃N₂SF

acetoxymethyl 7β-phenylacetamido-3-methyl-3-cephem-4-carboxylate