7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

Base Information

• Chemical Name: 7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester
• CAS No.: 36923-21-4
• Molecular Formula: C20H18N2O3S
• Molecular Weight: 366.441
• Hs Code.: 3003201900
• European Community (EC) Number: 813-561-9
• DSSTox Substance ID: DTXSID40534435
• Mol file: 36923-21-4.mol

Synonyms:36923-21-4;7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester;benzhydryl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;DTXSID40534435;BCP12091;AKOS015895935;C74905;Diphenylmethyl 7(c)micro-Amino-3-cephem-4-carboxylate;7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicaciddiphenylmethylester;DIPHENYLMETHYL 7-AMINO-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLATE;7-AICA;(6R,7R)-Benzhydryl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property of 7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 164.0 to 168.0 °C
• Refractive Index: 1.701
• Boiling Point: 587.751 °C at 760 mmHg
• PKA: 4.97±0.40(Predicted)
• Flash Point: 309.261 °C
• PSA: 97.93000
• Density: 1.397 g/cm³
• LogP: 3.08370
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Heated)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 366.10381361
• Heavy Atom Count: 26
• Complexity: 564

Purity/Quality:

99% ^*data from raw suppliers

Diphenylmethyl 7β-Amino-3-cephem-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=C(N2C(S1)C(C2=O)N)C(=O)OC(C3=CC=CC=C3)C4=CC=CC=C4
• Uses: An intermediate in the preparation of cephems: beta-lactam antibiotics.

Technology Process of 7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

There total 15 articles about 7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester 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: 92.6%

bis(diphenylmethyl) 7(R)-glutaroylaminoceph-3-em-4-carboxylate → diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (36923-21-4)

Guidance literature:

With pyridine; phosphorus pentachloride; In methanol; dichloromethane; at -50 - 0 ℃; Industrial scale;

DOI:10.1021/op010071y

Reference yield: 70.22%

(6R)-3ξ-hydroxy-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid benzhydryl ester (51762-51-7) → diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (36923-21-4)

Guidance literature:

With pyridine; dichlorotriphenylphosphorane; In propylene glycol; dichloromethane; at -15 - 28 ℃; for 5h; Solvent; Inert atmosphere;

Reference yield:

bis(diphenylmethyl) 3-exo-methylene-7(R)-glutaroylaminocepham-4-carboxylate 1(S)-oxide → diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (36923-21-4)

Guidance literature:

Multi-step reaction with 4 steps

1: ozone / dichloromethane / -65 - -55 °C / 413.73 Torr / Industrial scale

2: phosphorus trichloride / N,N-dimethyl-formamide / 5 h / -55 - 20 °C / Industrial scale

3: acetic acid; zinc / dichloromethane / 3 h / 20 °C / Industrial scale

4: phosphorus pentachloride; pyridine / dichloromethane; methanol / -50 - 0 °C / Industrial scale

With pyridine; phosphorus pentachloride; ozone; acetic acid; zinc; phosphorus trichloride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/op010071y

upstream raw materials:

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

diazodiphenylmethane

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

(6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Downstream raw materials:

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-carboxylate

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-hexenoylamino>-3-cephem-4-carboxylate

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-3-cyclopropyl-2-propenoylamino>-3-cephem-4-carboxylate

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-3-cyclopentyl-2-propenoylamino>-3-cephem-4-carboxylate

Refernces

• 1、 Lin, Ho-Shen,Rampersaud, Ashraff A.,Flokowitsch, Jane E.,Alborn, William E.,Wu, Ernie C. Y.,Preston, David A.. "Synthesis and in Vitro Evaluation of New Cephalosporins Exhibiting Antimicrobial Activity Against Gram-Positive Bacteria, in Particular Methicillin-Resistant Staphylococci". . p. 833 - 846. Retrieved 2007/10/03.