(6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid

Base Information

• Chemical Name: (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• CAS No.: 79750-46-2
• Molecular Formula: C₁₆H₁₇N₃O₄S
• Molecular Weight: 347.395
• European Community (EC) Number: 892-606-4
• UNII: 4HFX5Q5ET4
• DSSTox Substance ID: DTXSID80554692
• Nikkaji Number: J582.928C
• Mol file: 79750-46-2.mol

Synonyms:79750-46-2;DELTA2-CEPHALEXIN;Cephalexin Impurity F;(6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid;(6R,7R)-7-((R)-2-Amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid;| currency2-Cephalexin;?2-Cephalexin;(6R,7R)-7-[(R)-2-Amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid;(6R,7R)-7-{[(2R)-2-Amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid;Cephalexin, Delta2-;4HFX5Q5ET4;DTXSID80554692;5-Thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid, 7-[(aminophenylacetyl)amino]-3-methyl-8-oxo-, [6R-[6alpha,7beta(R*)]]-;5-Thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid, 7-[[(2R)-aminophenylacetyl]amino]-3-methyl-8-oxo-, (6R,7R)-;7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid, (6R,7R)-

Chemical Property of (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid

Chemical Property:

• Boiling Point: 724.4±60.0 °C(Predicted)
• PKA: 2.59±0.60(Predicted)
• PSA: 141.52000
• Density: 1.49±0.1 g/cm3(Predicted)
• LogP: 1.92180
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly, Heated), Methanol (Slightly), Water (Sl
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 347.09397721
• Heavy Atom Count: 24
• Complexity: 588

Purity/Quality:

98% ^*data from raw suppliers

Δ2-Cephalexin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CSC2C(C(=O)N2C1C(=O)O)NC(=O)C(C3=CC=CC=C3)N
• Isomeric SMILES: CC1=CS[C@@H]2[C@@H](C(=O)N2C1C(=O)O)NC(=O)[C@@H](C3=CC=CC=C3)N
• Uses: Δ2-Cephalexin is an isomeric impurity of the semi-synthetic antibiotic Cephalexin (C256800). Δ2-Cephalexin (Cefalexin EP Impurity F) is an isomeric impurity of the semi-synthetic antibiotic Cephalexin (C256800).

Technology Process of (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid

There total 11 articles about (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic 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: 40.3%

cefalexin (15686-71-2,27726-35-8,34632-04-7,79814-91-8,108260-04-4) → (6R,7R)-3-methyl-7-[(R)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid (79750-46-2)

Guidance literature:

cefalexin; With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane; at -30 - 25 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at 20 - 25 ℃; for 0.5h; Reagent/catalyst; Solvent; Catalytic behavior; Inert atmosphere;

Reference yield:

N-tert-butyloxycarbonylcefradine (57872-62-5) → Cefradine (30959-67-2,38821-53-3,52842-45-2) + cefalexin (15686-71-2,27726-35-8,34632-04-7,79814-91-8,108260-04-4) + (6R,7R)-3-methyl-7-[(R)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid (79750-46-2) + Δ2-cefradine

Guidance literature:

With 200-400 mesh; anion exchange resin Bio-Rad AG-3; acetic anhydride; trifluoroacetic acid; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) pyridine, r.t., 12 h, 2.) 12 h;

DOI:10.1002/ardp.19943270405

Reference yield:

(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 (31461-05-9) + (R)-2-(tert-butoxycarbonylamino)-2-(cyclohexa-1,4-dienyl)acetic acid (57872-59-0,57410-95-4) → Cefradine (30959-67-2,38821-53-3,52842-45-2) + cefalexin (15686-71-2,27726-35-8,34632-04-7,79814-91-8,108260-04-4) + (6R,7R)-3-methyl-7-[(R)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid (79750-46-2) + Δ2-cefradine

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1002/ardp.19943270405

upstream raw materials:

(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

Boc-D-Phg-OH

(R)-2-(tert-butoxycarbonylamino)-2-(cyclohexa-1,4-dienyl)acetic acid

N-tert-butyloxycarbonylcefradine

Refernces

• 1、 Hendrix,Roets,Bervoets,Thomas,Pijcke,Busson,Janssen,Hoogmartens. "Synthesis of potential impurities of cefalexin and cefradine". . p. 215 - 219. Retrieved 2007/10/02.