(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

Base Information

• Chemical Name: (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
• CAS No.: 609812-77-3
• Molecular Formula: C₄₀H₃₂N₂O₇S
• Molecular Weight: 684.769
• Mol file: 609812-77-3.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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: 28.0%

2-[(2-oxo-2H-chromen-7-yl)oxy]acetaldehyde (16851-02-8) + 4-(diphenylmethoxycarbonyl)-7β-phenylacetamidoceph-3-en-3-ylmethylphosphonium iodide (107550-89-0) → (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 (609812-77-3)

Guidance literature:

4-(diphenylmethoxycarbonyl)-7β-phenylacetamidoceph-3-en-3-ylmethylphosphonium iodide; With sodium hydroxide; In dichloromethane; at 20 ℃; for 0.5h;

2-[(2-oxo-2H-chromen-7-yl)oxy]acetaldehyde; In dichloromethane; at 20 ℃;

DOI:10.1021/ja036126o

Reference yield:

7-hydroxy-2H-chromen-2-one (93-35-6) → (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 (609812-77-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 82 percent / K₂CO₃ / dimethylformamide / 12 h / 115 °C

2.1: 63 percent / aq. HCl / CHCl₃ / 0.5 h / 0 °C

3.1: aq. NaOH / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 28 percent / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium hydroxide; potassium carbonate; In dichloromethane; chloroform; N,N-dimethyl-formamide; 3.2: Wittig reaction;

DOI:10.1021/ja036126o

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)-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 (609812-77-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaI / acetone / 1 h / 20 °C

2.1: 0.715 g / ethyl acetate / 12 h

3.1: aq. NaOH / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 28 percent / CH₂Cl₂ / 20 °C

With sodium hydroxide; sodium iodide; In dichloromethane; ethyl acetate; acetone; 3.2: Wittig reaction;

DOI:10.1021/ja036126o

upstream raw materials:

2-[(2-oxo-2H-chromen-7-yl)oxy]acetaldehyde

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

7-hydroxy-2H-chromen-2-one

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

Downstream raw materials:

(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

(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 benzhydryl ester

(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