Sulbenicillin sodium

Base Information

• Chemical Name: Sulbenicillin sodium
• CAS No.: 28002-18-8
• Deprecated CAS: 34861-62-6
• Molecular Formula: C₁₆H₁₆N₂O₇S₂*2Na
• Molecular Weight: 458.424
• European Community (EC) Number: 248-769-3
• DSSTox Substance ID: DTXSID2048618
• Wikidata: Q27114803
• Mol file: 28002-18-8.mol

Synonyms:alpha-Sulfobenzylpenicillin, Disodium;Disodium alpha Sulfobenzylpenicillin;Disodium alpha-Sulfobenzylpenicillin;I.M., Kedacillin;Kedacillin I.M.;Sulbenicillin;Sulfobenzylpenicillin

Chemical Property of Sulbenicillin sodium

Chemical Property:

• PSA: 180.42000
• LogP: -0.02050
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 458.01943176
• Heavy Atom Count: 29
• Complexity: 736

Purity/Quality:

99% ^*data from raw suppliers

Sulbenicillinsodium 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)S(=O)(=O)[O-])C(=O)[O-])C.[Na+].[Na+]
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)S(=O)(=O)[O-])C(=O)[O-])C.[Na+].[Na+]
• Therapeutic Function: Antibacterial

Technology Process of Sulbenicillin sodium

There total 18 articles about Sulbenicillin sodium 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: 94.9%

Sulbenicillin (58569-36-1) → (2S,5R,6R)-3,3-dimethyl-6-(2-phenyl-2-sulfoacetylamino)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt (28002-18-8,36417-90-0,36417-91-1,37544-62-0,76194-04-2)

Guidance literature:

With sodium isooctanoate; In acetone; at 10 - 20 ℃; for 1.5h;

Reference yield: 91.5%

6-Aminopenicillanic Acid (551-16-6) + 6,6-dimethyl-3-phenyl-1,5,2-dioxathiane-4-one-2,2-dioxide → (2S,5R,6R)-3,3-dimethyl-6-(2-phenyl-2-sulfoacetylamino)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt (28002-18-8,36417-90-0,36417-91-1,37544-62-0,76194-04-2)

Guidance literature:

6-Aminopenicillanic Acid; With N,O-bis-(trimethylsilyl)-acetamide; In acetone; at 30 - 35 ℃; for 3h;

6,6-dimethyl-3-phenyl-1,5,2-dioxathiane-4-one-2,2-dioxide; In acetone; at 40 - 45 ℃; for 5h;

With sodium 2-ethylhexanoic acid; In water; acetone; at 5 - 20 ℃; for 2h; Temperature;

Reference yield: 88.1%

6-Aminopenicillanic Acid (551-16-6) + racemic α-sulfophenylacetic acid (41360-32-1) → (2S,5R,6R)-3,3-dimethyl-6-(2-phenyl-2-sulfoacetylamino)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt (28002-18-8,36417-90-0,36417-91-1,37544-62-0,76194-04-2)

Guidance literature:

racemic α-sulfophenylacetic acid; With triethanolamine; 1,1'-carbonyldiimidazole; In dichloromethane; toluene; at -10 ℃; for 1.5h;

6-Aminopenicillanic Acid; In dichloromethane; water; isopropyl alcohol; acetone; toluene; at -5 - 10 ℃; for 0.75h;

With sodium hydroxide; In water; pH=6 - 7; Concentration; Solvent;

upstream raw materials:

6-Aminopenicillanic Acid

2-sulpho-2-phenylacetyl chloride

phenylacetic acid

racemic α-sulfophenylacetic acid

Refernces

• 1、 -. "Preparation method of D-(-)-alpha-sulbenicillin sodium". Paragraph 0025-0031. . Retrieved 2018/08/04.
• 2、 -. "Sulbenicillin sodium intermediate and method for preparing sulbenicillin sodium therefrom". Paragraph 0071-0076. . Retrieved 2018/11/22.