2,2,2-Trichloroethyl3-methyl-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicydo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: 2,2,2-Trichloroethyl3-methyl-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicydo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 28180-80-5
• Molecular Formula: C18H17 Cl3 N2 O4 S
• Molecular Weight: 463.769
• Mol file: 28180-80-5.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-methyl-8-oxo-7-(2-phenylacetamido)-, 2,2,2-trichloroethyl ester (8CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-methyl-8-oxo-7-[(phenylacetyl)amino]-, 2,2,2-trichloroethyl ester, (6R,7R)-(9CI); 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-methyl-8-oxo-7-[(phenylacetyl)amino]-, 2,2,2-trichloroethyl ester,(6R-trans)-; Ethanol, 2,2,2-trichloro-,3-methyl-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(8CI); 2,2,2-Trichlorethyl3-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate; 3-Cephem-4-carboxylicacid 2,2,2-trichloroethyl ester, 3-methyl-7b-phenylacetoamido-;7-Phenylacetamido-3-methyl-3-cephem-4-carboxylic acid trichloroethyl ester

Chemical Property of 2,2,2-Trichloroethyl3-methyl-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicydo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

• PSA: 101.01000
• LogP: 3.14520

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,2,2-Trichloroethyl3-methyl-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicydo[4.2.0]oct-2-ene-2-carboxylate

There total 3 articles about 2,2,2-Trichloroethyl3-methyl-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicydo[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: 72.0%

(6R,7R)-3-Methyl-5,8-dioxo-7-phenylacetylamino-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester (30200-16-9) → (6R,7R)-2,2,2-trichloroethyl 3-methyl-7-phenylacetamidoceph-3-em-4-carboxylate (28180-80-5)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1080/00397919108021575

Reference yield: 71.0%

2,2,2-trichloroethyl (1S,3S,5R,6R)-6-phenylacetamido-2,2-dimethylpenam-3-carboxylate, 1-oxide (39879-59-9) → (6R,7R)-2,2,2-trichloroethyl 3-methyl-7-phenylacetamidoceph-3-em-4-carboxylate (28180-80-5)

Guidance literature:

With dipyridinium phosphate; In various solvent(s); for 4h;

Reference yield:

→ (6R,7R)-2,2,2-trichloroethyl 3-methyl-7-phenylacetamidoceph-3-em-4-carboxylate (28180-80-5)

Guidance literature:

Sulfoxidoester 3b (Umlagerung);

DOI:10.1021/jo00808a021

upstream raw materials:

2,2,2-trichloroethyl (1S,3S,5R,6R)-6-phenylacetamido-2,2-dimethylpenam-3-carboxylate, 1-oxide

(6R,7R)-3-Methyl-5,8-dioxo-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Downstream raw materials:

(2S,6R,7R)-2,2,2-trichloroethyl 2-methoxy-3-methyl-7-phenylacetamidoceph-3-em-4-carboxylate

2,2,2-trichloroethyl 5-methylthiazole-4-carboxylate

2,2,2-trichloroethyl 2-methoxycarbonyl-5-methylthiazole-4-carboxylate

methyl α-methoxy-5-methyl-α-phenylacetamido-4-(2,2,2-trichloroethoxycarbonylthiazol)-2-ylacetate

Refernces

• 1、 Kazimierczak, Jerzy,Mikolajczyk, Jerzy,Cieslak, Jerzy. "CEPHALOSPORINS. PART III. REARRANGEMENTS OF 6-HALOPENICILLIN 1-OXIDES INTO 7-HALOCEPHALOSPORANIC ACIDS". . p. 3 - 8. Retrieved 2007/10/02.