(6R,7R)-3-Hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenyl methyl ester

Base Information

• Chemical Name: (6R,7R)-3-Hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenyl methyl ester
• CAS No.: 54639-48-4
• Molecular Formula: C28H24N2O5S
• Molecular Weight: 500.575
• Hs Code.: 2941905990
• Mol file: 54639-48-4.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-hydroxy-8-oxo-7-[(phenylacetyl)amino]-, diphenylmethyl ester, (6R,7R)-(9CI);Diphenylmethyl (6R,7R)-3-hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;

Chemical Property of (6R,7R)-3-Hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenyl methyl ester

Chemical Property:

• Appearance/Colour: White or off-white crysalline powder
• Vapor Pressure: 1.73E-21mmHg at 25°C
• Refractive Index: 1.725
• Boiling Point: 777.1 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 423.8 °C
• PSA: 121.24000
• Density: 1.42 g/cm³
• LogP: 4.06020
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

3(6R,7R)-Hydroxy-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidDiphenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3(6R,7R)--Hydroxy-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Diphenylmethyl Ester is a useful synthetic intermediate. It was used to prepare cephalosporin-derived inhibitors. It can also be used to synthesize Ceftaroline Fosamil which is a cephalosporin antibiotic.

Technology Process of (6R,7R)-3-Hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenyl methyl ester

There total 13 articles about (6R,7R)-3-Hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenyl methyl ester 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: 79.0%

(6R,7R)-3-Benzhydryloxy-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (131857-37-9) → (6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (54639-48-4)

Guidance literature:

With trifluoroacetic acid; In acetic acid; for 5h; Ambient temperature;

DOI:10.1246/bcsj.68.1385

Reference yield: 61.0%

1-<3-chloro-1-(diphenylmethyloxycarbonyl)-2-hydroxy-1-propen-1-yl>-3-(phenylacetamido)-4-(phenylsulfonylthio)-2-azetidinone (164201-44-9) → (6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (54639-48-4)

Guidance literature:

With pyridine; bismuth(III) chloride; tin; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1246/bcsj.68.1385

Reference yield: 15.0%

diphenylmethyl 2-(3-benzyl-6-oxo-2-thia-4,7-diazabicyclo<3.2.0>hept-3-en-7-yl)-4-chloro-3-morpholino-2-butenoate → (6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (54639-48-4)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; methanol; for 1.5h; Ambient temperature;

DOI:10.1246/bcsj.68.1385

upstream raw materials:

(6R)-3-methylene-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester

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

1-<3-chloro-1-(diphenylmethyloxycarbonyl)-2-hydroxy-1-propen-1-yl>-3-(phenylacetamido)-4-(phenylsulfonylthio)-2-azetidinone

1-<3-chloro-2-(diphenylmethyloxy)-1-(diphenylmethyloxycarbonyl)-1-propen-1-yl>-3-(phenylacetamido)-4-(phenylsulfonylthio)-2-azetidinone

Downstream raw materials:

(6R)-2-methyl-3,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid benzhydryl ester

(6R)-8-oxo-7t-(2-phenyl-acetylamino)-3-(toluene-4-sulfonyloxy)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

N-((6R)-3,8-dioxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-7t-yl)-2-phenyl-acetamide

(6R)-3-methoxyimino-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid benzhydryl ester

Refernces

• 1、 Scartazzini,Bickel. "New β lactam antibiotics. Derivatives of 7 amino 3 hydroxyceph 3 em 4 carboxylic acid". . p. 1919 - 1934. Retrieved 2007/10/07.