Sulbactam pivoxil

Base Information

• Chemical Name: Sulbactam pivoxil
• CAS No.: 69388-79-0
• Molecular Formula: C14H21NO7S
• Molecular Weight: 347.389
• UNII: 2X0WTA96KX
• Nikkaji Number: J19.106J
• NCI Thesaurus Code: C96733
• ChEMBL ID: CHEMBL423875
• Mol file: 69388-79-0.mol

Synonyms:CP 47,904;CP-47,904;CP-47904;sulbactam pivoxil;sulbactam pivoxyl

Chemical Property of Sulbactam pivoxil

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.538
• Boiling Point: 537.534 °C at 760 mmHg
• PKA: -3.75±0.60(Predicted)
• Flash Point: 278.891 °C
• PSA: 115.43000
• Density: 1.371 g/cm³
• LogP: 1.22910
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 347.10387318
• Heavy Atom Count: 23
• Complexity: 654

Purity/Quality:

99% up by HPLC ^*data from raw suppliers

SulbactamPivoxil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)OCOC(=O)C(C)(C)C)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)OCOC(=O)C(C)(C)C)C
• Uses: Sulbactam Pivoxil is a prodrug of the semi-synthetic β-lactamase inhibitor Sulbactam (S699195).

Technology Process of Sulbactam pivoxil

There total 10 articles about Sulbactam pivoxil 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: 85.0%

Chloromethyl pivalate (18997-19-8) + sodium sulbactam (69388-84-7) → (pivaloyloxy)methyl 6,6-dihydropenicillanate S,S-dioxide (69388-79-0)

Guidance literature:

In dimethyl sulfoxide; at 20 - 25 ℃; for 18h;

DOI:10.1016/S0014-827X(00)00005-7

Reference yield: 67.0%

(2S,6S)-6-Bromo-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (76454-58-5,76646-89-4) → (S)-3,3-Dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (69388-79-0)

Guidance literature:

With tetraethylammonium tosylate; In methanol; acetic acid; N,N-dimethyl-formamide; at 0 - 10 ℃; electroreduction;

DOI:10.1248/cpb.36.1976

Reference yield:

(pivaloyloxy)methyl 6,6-dibromopenicillanate S,S-dioxide (76454-57-4) → (pivaloyloxy)methyl 6,6-dihydropenicillanate S,S-dioxide (69388-79-0)

Guidance literature:

With sodium hydrogencarbonate; palladium; In methanol; water; ethyl acetate;

upstream raw materials:

Chloromethyl pivalate

sodium sulbactam

(pivaloyloxy)methyl 6,6-dibromopenicillanate S,S-dioxide

tri-n-butyl-tin hydride

Refernces

• 1、 English,Girard,Jasys,Martingano,Kellogg. "Orally effective acid prodrugs of the β-lactamase inhibitor sulbactam". . p. 344 - 347. Retrieved 2007/10/02.
• 2、 Ikeda,Tsukamoto,Nishiguchi,Hirashima. "A novel synthetic method for penicillanic acid derivatives by electroreduction". . p. 1976 - 1981. Retrieved 2007/10/02.