7-[[2-(Furan-2-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: 7-[[2-(Furan-2-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 56271-94-4
• Molecular Formula: C15H15 N3 O7 S
• Molecular Weight: 381.366
• European Community (EC) Number: 260-086-2
• Mol file: 56271-94-4.mol

Synonyms:56271-94-4;PD164098;FT-0665941

Chemical Property of 7-[[2-(Furan-2-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 3Pa at 20℃
• PKA: 2.75±0.50(Predicted)
• PSA: 170.46000
• Density: 1.71±0.1 g/cm3(Predicted)
• LogP: 0.13920
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Water Solubility.: 1mg/L
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 381.06307100
• Heavy Atom Count: 26
• Complexity: 693

Purity/Quality:

99.9% ^*data from raw suppliers

DescarbamoylCefuroxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CON=C(C1=CC=CO1)C(=O)NC2C3N(C2=O)C(=C(CS3)CO)C(=O)O
• Uses: Descarbamoyl Cefuroxime (Cefuroxime Sodium EP Impurity A) is a degradation product of Cefuroxime, and an intermediate for the synthesis of Cephalosporin antibiotics A degradation product of Cefuroxime, and an intermediate for the synthesis of Cephalosporin antibiotics

Technology Process of 7-[[2-(Furan-2-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 12 articles about 7-[[2-(Furan-2-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-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: 89.1%

(Z)-2-methoxyimino-2-(furyl-2-yl)acetic acid ammonium salt (97148-39-5) + (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) → (6R,7R)-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (56271-94-4)

Guidance literature:

(Z)-2-methoxyimino-2-(furyl-2-yl)acetic acid ammonium salt; With N,N-dimethyl acetamide; phosphorus pentachloride; In dichloromethane; at -30 - -10 ℃; for 1.33333h;

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; With sodium hydroxide; In dichloromethane; water; for 2h; pH=6.5 - 7;

Reference yield: 80.6%

sodium 3-debenzoyl-acetyl-cefuroxime (57847-71-9) → (6R,7R)-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (56271-94-4)

Guidance literature:

With hydrogenchloride; ethylenediaminetetraacetic acid; acetic acid; sodium hydroxide; In methanol; dichloromethane; water; at -20 - 5 ℃; for 1h; pH=2 - 6;

Reference yield:

7-[(Z)-2-Furyl-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephalosporanic acid (39685-31-9) → (6R,7R)-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (56271-94-4)

Guidance literature:

In water; at 0 - 10 ℃; for 0.5h;

upstream raw materials:

Cefuroxime

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2-furyl(methoxyimino)acetyl chloride

7-Aminocephalosporanic acid

Downstream raw materials:

Cefuroxime