5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 8-oxo-7-[(phenylacetyl)amino]-3-[[(trifluoromethyl)sulfonyl]oxy]-, diphenylmethyl ester, (6R,7R)-

Base Information

• Chemical Name: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 8-oxo-7-[(phenylacetyl)amino]-3-[[(trifluoromethyl)sulfonyl]oxy]-, diphenylmethyl ester, (6R,7R)-
• CAS No.: 122553-60-0
• Molecular Formula: C29H23F3N2O7S2
• Molecular Weight: 632.638
• Mol file: 122553-60-0.mol

Synonyms:

Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 8-oxo-7-[(phenylacetyl)amino]-3-[[(trifluoromethyl)sulfonyl]oxy]-, diphenylmethyl ester, (6R,7R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 8-oxo-7-[(phenylacetyl)amino]-3-[[(trifluoromethyl)sulfonyl]oxy]-, diphenylmethyl ester, (6R,7R)-

There total 2 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 8-oxo-7-[(phenylacetyl)amino]-3-[[(trifluoromethyl)sulfonyl]oxy]-, diphenylmethyl ester, (6R,7R)- 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: 96.0%

trifluoromethylsulfonic anhydride (358-23-6) + (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) → (6R,7R)-benzhydryl 8-oxo-7-(2-phenylacetamido)-3-(((trifluoromethyl)sulfonyl)oxy)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (122553-60-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -20 ℃; for 1h;

Reference yield: 91.0%

(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) + trifluoroacetic anhydride (407-25-0) → (6R,7R)-benzhydryl 8-oxo-7-(2-phenylacetamido)-3-(((trifluoromethyl)sulfonyl)oxy)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (122553-60-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/jo001429b

Reference yield: 95.0%

(6R,7R)-benzhydryl 8-oxo-7-(2-phenylacetamido)-3-(((trifluoromethyl)sulfonyl)oxy)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (122553-60-0) → (6R,7R)-benzhydryl 3-chloro-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (63821-56-7)

Guidance literature:

With lithium chloride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/jo00281a048

upstream raw materials:

trifluoromethylsulfonic anhydride

(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

trifluoroacetic anhydride

Downstream raw materials:

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

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

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

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