2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 117467-28-4
• Molecular Formula: C25H28N6O7S3
• Molecular Weight: 620.731
• Hs Code.: 2941905990
• European Community (EC) Number: 688-157-7
• NCI Thesaurus Code: C47434
• ChEMBL ID: CHEMBL3348868
• Mol file: 117467-28-4.mol

Synonyms:(-)-(6R,7R)-2,2-dimethylpropionyloxymethyl 7-((Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido)-3-((Z)-2-(4-methylthiazol-5-yl)ethenyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate;7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-(2-(4-methylthiazol-5-yl)ethenyl)cephem-4-carboxylic acid pivaloyloxymethyl ester;CDTR-PI;cefditoren pivoxil;ME 1207;ME-1207;Spectracef

Chemical Property of 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

• Appearance/Colour: off-white powder
• Melting Point: 207-209 °C
• Refractive Index: 1.71
• PKA: 8.08±0.60(Predicted)
• PSA: 257.18000
• Density: 1.55 g/cm³
• LogP: 3.20810
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 12
• Exact Mass: 620.11816077
• Heavy Atom Count: 41
• Complexity: 1160

Purity/Quality:

98% ^*data from raw suppliers

Cefditoren Pivoxil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC=N1)C=CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)OCOC(=O)C(C)(C)C
• Isomeric SMILES: CC1=C(SC=N1)C=CC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)OCOC(=O)C(C)(C)C
• Recent ClinicalTrials: Pilot Study of Cefditoren Pivoxil in COVID-19 Patients With Mild to Moderate Pneumonia
• Recent NIPH Clinical Trials: Study of the clinical efficacy and number of days of administration of cefditoren pivoxil in the treatment of adult acute uncomplicated cystitis
• Description: Cefditoren pivoxil is an orally active third generation cephalosporin introduced in Japan as a treatment for a broad range of bacterial infections including dermatological and other community acquired infections. Cefditoren pivoxil is reported to have a broad spectrum of activity against both Gram-positive and Gramnegative bacteria, more potent than many other existing agents of its class. In particular, it shows the highest therapeutic activity against S. pneumoniae and S. marcescens infections. It exhibits resistance to β-lactamase hydrolysis typical of third generation cephalosporins. As a prodrug of cefditoren, it is readily absorbed through GI tract and has low toxicity and side effects. Cefditoren pivoxil is an orally bioavailable prodrug form of the broad-spectrum cephalosporin antibiotic cefditoren. Cefditoren pivoxil is hydrolyzed by intestinal wall esterases to form cefditoren. Cefditoren pivoxil is effective against systemic S. aureus, E. coli, K. pneumoniae, P. mirabilis, or S. marcescens infections in mice with ED50 values of 10, 2.5, 11, 4.4, and 11 mg/kg, respectively. Formulations containing cefditoren pivoxil were previously used in the treatment of acute bacterial exacerbations of chronic bronchitis and community-acquired pneumonia.
• Uses: Cefditoren Pivoxil is an antibacterial and is a third generation cephalosporin. An antibacterial. Third generation cephalosporin antidepressant
• Therapeutic Function: Antibiotic
• Clinical Use: It has been advocated for community-acquired upper and lower respiratory tract infections and skin infections.

Technology Process of 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 23 articles about 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 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: 98.75%

iodomethyl pivaloate (53064-79-2) + cefditoren (104145-95-1) → cefditoren pivoxil (117467-28-4)

Guidance literature:

cefditoren; With pyridine; In N,N-dimethyl-formamide; at -10 ℃;

iodomethyl pivaloate; at -10 ℃; for 1h;

Reference yield: 96.84%

iodomethyl pivaloate (53064-79-2) + C24H26N6O7S3 → cefditoren pivoxil (117467-28-4)

Guidance literature:

C₂₄H₂₆N₆O₇S₃; With tetraethylammonium hydroxide; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 2h;

iodomethyl pivaloate; With pyridine; In 1-methyl-pyrrolidin-2-one; at 0 - 20 ℃; for 1h;

With t-butyldimethylsiyl triflate; In 1-methyl-pyrrolidin-2-one; at 0 ℃; for 0.25h;

Reference yield: 95.3%

iodomethyl pivaloate (53064-79-2) + 7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt (104146-53-4) → cefditoren pivoxil (117467-28-4)

Guidance literature:

With tetrabutylammomium bromide; In dichloromethane; water; at 0 - 25 ℃; for 2h; Reagent/catalyst;

upstream raw materials:

Chloromethyl pivalate

7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt

4-methyl-1,3-thiazole-5-carbaldehyde

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Refernces

• 1、 -. "Preparation method of high-purity cefditoren pivoxil". Paragraph 0050-0075. . Retrieved 2020/01/25.
• 2、 -. "Method for synthesizing cefditoren pivoxil". Paragraph 0059; 0065-0068; 0074; 0075; 0081; 0082; 0088-0094. . Retrieved 2019/01/20.