Cefathiamidine Impurity 1

Base Information

• Chemical Name: Cefathiamidine Impurity 1
• CAS No.: 26973-80-8
• Molecular Formula: C12H13 Br N2 O6 S
• Molecular Weight: 393.215
• UNII: 4N6P66J4H2
• DSSTox Substance ID: DTXSID90514080
• Nikkaji Number: J1.583.399H
• Wikidata: Q82374214
• Mol file: 26973-80-8.mol

Synonyms:26973-80-8;Cefathiamidine Impurity 1;7-Bromoacetylaminocephalosporanic acid;(6R,7R)-3-(Acetyloxymethyl)-7-[(2-bromoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-(alpha-Bromoacetamido)cephalosporanic acid;(6R,7R)-3-(acetoxymethyl)-7-(2-bromoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;SCHEMBL2334986;DTXSID90514080;4N6P66J4H2;7-(2-Bromoacetamido)cephalosporanic acid;(6R, 7R)-3-(acetyloxymethyl)-7-[(2-bromoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-3-(acetoxymethyl)-7-(2-bromoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid;(6R,7R)-3-[(Acetyloxy)methyl]-7-(2-bromoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-3-[(Acetyloxy)methyl]-7-[(2-bromoacetyl)amino]-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, 3-[(acetyloxy)methyl]-7-[(2-bromoacetyl)amino]-8-oxo-, (6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[(bromoacetyl)amino]-8-oxo-, (6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[(bromoacetyl)amino]-8-oxo-, (6R-trans)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-(2-bromoacetamido)-3-(hydroxymethyl)-8-oxo-, acetate (ester)

Chemical Property of Cefathiamidine Impurity 1

Chemical Property:

• Boiling Point: 711.2±60.0 °C(Predicted)
• PKA: 2.67±0.50(Predicted)
• PSA: 141.80000
• Density: 1.81±0.1 g/cm3(Predicted)
• LogP: 0.46120
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform, Dichloromethane, Dimethyl Sulfoxide
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 391.96777
• Heavy Atom Count: 22
• Complexity: 578

Purity/Quality:

99% ^*data from raw suppliers

7-BromoacetylaminocephalosporanicAcid ^*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)CBr)SC1)C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CBr)SC1)C(=O)O
• Uses: An analog of glutaryl-7-amino cephalosporanic acid (GL-7-ACA). Can inhibit and specifically alkylate GL-7-ACA acylase (C130) from Pseudomonas sp.130 by forming a carbon-carbon bond between BA-7-ACA and the C-2 on indole ring of Trp-β4 residue of C130.

Technology Process of Cefathiamidine Impurity 1

There total 2 articles about Cefathiamidine Impurity 1 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:

2-Bromoacetyl bromide (598-21-0) + 7-Aminocephalosporanic acid (957-68-6) → N-bromoacetyl-7-aminocephalosporanic acid (26973-80-8)

Guidance literature:

With sodium hydrogencarbonate;

DOI:10.1021/jm00270a025

Reference yield:

→ bromoacetylaminocephalosporanic acid (26973-80-8)

Guidance literature:

/BRN= 622637/, CH2BrCOCl, NaHCO3, HCl(pH1?2);

Reference yield: 42.0%

N-bromoacetyl-7-aminocephalosporanic acid (26973-80-8) + 2-Amino-5-mercapto-1,3,4-thiadiazole (2349-67-9) → 7-[2-(4,5-dihydro-5-imino-1,3,4-thiadiazol-2-ylthio)acetamido]cephalosporanic acid (60458-29-9)

Guidance literature:

In acetone;

upstream raw materials:

2-Bromoacetyl bromide

7-Aminocephalosporanic acid

Downstream raw materials:

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

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

cephapirin

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