Cefaloram

Base Information

• Chemical Name: Cefaloram
• CAS No.: 859-07-4
• Molecular Formula: C18H18 N2 O6 S
• Molecular Weight: 390.417
• European Community (EC) Number: 212-725-1
• UNII: K3086GQJ9Z
• DSSTox Substance ID: DTXSID9046106
• Nikkaji Number: J7.146C
• Wikidata: Q27281875
• NCI Thesaurus Code: C76156
• ChEMBL ID: CHEMBL1700858
• Mol file: 859-07-4.mol

Synonyms:cefaloram;cefaloram, potassium salt;cefaloram, sodium salt;cephaloram

Chemical Property of Cefaloram

Chemical Property:

• Vapor Pressure: 3.58E-23mmHg at 25°C
• Melting Point: 160-162 °C (decomp)
• Boiling Point: 742.8°C at 760 mmHg
• PKA: 2.68±0.50(Predicted)
• Flash Point: 403°C
• PSA: 138.31000
• Density: 1.48g/cm³
• LogP: 0.85960
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 390.08855747
• Heavy Atom Count: 27
• Complexity: 685

Purity/Quality:

98%Min ^*data from raw suppliers

CEFALORAM 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CC3=CC=CC=C3)SC1)C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CC3=CC=CC=C3)SC1)C(=O)O

Technology Process of Cefaloram

There total 11 articles about Cefaloram 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: 96.0%

7-Aminocephalosporanic acid (957-68-6) + phenylacetyl chloride (103-80-0) → cephaloram (859-07-4)

Guidance literature:

7-Aminocephalosporanic acid; With sodium carbonate; In water; acetone; at -5 ℃; for 0.166667h;

phenylacetyl chloride; In water; acetone; for 4h;

With hydrogenchloride; In water; ethyl acetate; acetone; pH=3 - 3.5;

DOI:10.1021/op900063e

Reference yield: 93.0%

(6R,7R)-benzhydryl 3-(acetyloxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (41128-81-8) → cephaloram (859-07-4)

Guidance literature:

With trifluoroacetic acid; In various solvent(s); at 45 ℃; for 1h;

DOI:10.1021/jo00011a034

Reference yield: 88.0%

(R)-3-Acetoxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester (108521-99-9) → (R)-3-Acetoxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (859-07-4)

Guidance literature:

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.416667h;

DOI:10.1016/S0040-4039(00)96512-2

upstream raw materials:

7-aminocephalosporanic acid

phenylacetyl chloride

3-Acetoxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R,7R)-benzhydryl 3-(acetyloxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Downstream raw materials:

(6R,7R)-benzhydryl 3-(acetyloxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

3-Acetoxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

3-formyl-7β-phenylacetylamino-ceph-2-em-4α-carboxylic acid diphenylmethyl ester

diphenylmethyl 7-phenylacetamido-3-acetyl-2-cephem-4-carboxylate

Refernces

• 1、 -. "PRODRUG INHIBITORS". Paragraph 00123. . Retrieved 2020/10/20.
• 2、 Majewski, Mark W.,Miller, Patricia A.,Miller, Marvin J.. "Studies at the ionizable position of cephalosporins and penicillins: Hydroxamates as substitutes for the traditional carboxylate group". . p. 292 - 296. Retrieved 2017/03/10.