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

Base Information

• Chemical Name: diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate
• CAS No.: 105890-09-3
• Molecular Formula: C₃₅H₃₇N₅O₈S₂
• Molecular Weight: 719.839
• Mol file: 105890-09-3.mol

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

Chemical Property of diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate

There total 1 articles about diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-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:

(6R,7R)-7-Amino-3-carbamoyloxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester; compound with toluene-4-sulfonic acid + (Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid (86978-24-7) → diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate (105890-09-3)

Guidance literature:

With methanesulfonyl chloride; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -50 deg C, 2.) CH₂Cl₂, -50 deg C;

DOI:10.7164/antibiotics.47.466

Reference yield: 87.2%

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate (105890-09-3) → cefcapene (135889-00-8)

Guidance literature:

With aluminium trichloride; In dichloromethane; at -30 ℃; for 0.5h;

DOI:10.7164/antibiotics.47.466

Reference yield:

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate (105890-09-3) → cefcapene pivoxil (105889-45-0)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / CH₂Cl₂; various solvent(s) / 2 h / 0 °C

2: 51.1 percent / K₂CO₃ / dimethylformamide / 1.5 h / -40 °C

3: 73 percent / trifluoroacetic acid / CH₂Cl₂ / 1.5 h / Ambient temperature

With potassium carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.47.466

upstream raw materials:

(Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid

Downstream raw materials:

cefcapene

((6R,7R)-3-((aminocarbonyl)oxy)methyl-7-((Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl)amino)-8-oxo-5-thio-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid(2,2-dimethyloxypropoxymethyl)ester

cefcapene pivoxil

Refernces