3-Iodomethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: 3-Iodomethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 51761-83-2
• Molecular Formula: C₂₉H₂₅IN₂O₄S
• Molecular Weight: 624.499
• Mol file: 51761-83-2.mol

Synonyms:3-Iodomethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property of 3-Iodomethyl-8-oxo-7-phenylacetylamino-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 3-Iodomethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 6 articles about 3-Iodomethyl-8-oxo-7-phenylacetylamino-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: 90.0%

7-phenylacetamido-3-chloromethylcephalosporanic acid benzhydryl ester → 3-Iodomethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (51761-83-2)

Guidance literature:

With Aliquat 336; sodium iodide; In water; toluene; for 6h; Ambient temperature; phosphate buffer pH 7;

Reference yield:

(6R,7R)-benzhydryl 3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (64308-63-0) → (6R,7R)-benzhydryl 3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (51761-83-2)

Guidance literature:

With sodium iodide; In acetone; at 20 ℃; for 1h;

DOI:10.1021/ja036126o

Reference yield:

phenylacetyl chloride (103-80-0) → (6R,7R)-benzhydryl 3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (51761-83-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine; triethylamine / acetonitrile / 0 - 20 °C

2: sodium iodide / acetone / 1 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; triethylamine; sodium iodide; In acetone; acetonitrile;

upstream raw materials:

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

phenylacetyl chloride

(6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxyli acid diphenylmethyl ester hydrochloride

Downstream raw materials:

4-(diphenylmethoxycarbonyl)-7β-phenylacetamidoceph-3-en-3-ylmethylphosphonium iodide

(6R,7R)-8-Oxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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