(6R,7R)-3-((E)-2-Methanesulfonyl-vinyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (6R,7R)-3-((E)-2-Methanesulfonyl-vinyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 180525-11-5
• Molecular Formula: C₂₉H₂₆N₂O₆S₃
• Molecular Weight: 594.733
• Mol file: 180525-11-5.mol

Synonyms:

Chemical Property of (6R,7R)-3-((E)-2-Methanesulfonyl-vinyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7R)-3-((E)-2-Methanesulfonyl-vinyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 3 articles about (6R,7R)-3-((E)-2-Methanesulfonyl-vinyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl 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:

(6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (123054-32-0) → (6R,7R)-3-((E)-2-Methanesulfonyl-vinyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (180525-11-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Pd₂dba3, TFP, ZnCl₂, NMP / 48 h / Ambient temperature

2: p-TsOH / acetonitrile / Ambient temperature

3: NaHSO₃ / tetrahydrofuran; H₂O

With 1-methyl-pyrrolidin-2-one; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; toluene-4-sulfonic acid; sodium hydrogensulfite; zinc(II) chloride; In tetrahydrofuran; water; acetonitrile;

DOI:10.1016/S0960-894X(96)00285-5

Reference yield:

(6R,7R)-7-tert-Butoxycarbonylamino-3-((E)-2-methanesulfonyl-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (180525-07-9) → (6R,7R)-3-((E)-2-Methanesulfonyl-vinyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (180525-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / acetonitrile / Ambient temperature

2: NaHSO₃ / tetrahydrofuran; H₂O

With toluene-4-sulfonic acid; sodium hydrogensulfite; In tetrahydrofuran; water; acetonitrile;

DOI:10.1016/S0960-894X(96)00285-5

Reference yield:

2-thienylacetic acid chloride (39098-97-0) + (6R,7R)-7-Amino-3-((E)-2-methanesulfonyl-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester → (6R,7R)-3-((E)-2-Methanesulfonyl-vinyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (180525-11-5)

Guidance literature:

With sodium hydrogensulfite; In tetrahydrofuran; water; Yield given;

DOI:10.1016/S0960-894X(96)00285-5

upstream raw materials:

2-thienylacetic acid chloride

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

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