benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 182268-38-8
• Molecular Formula: C₂₃H₂₂N₂O₅S
• Molecular Weight: 438.504
• Mol file: 182268-38-8.mol

Synonyms:benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property of benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 8 articles about benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 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: 89.0%

benzyl (-)-(6S,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182268-34-4) + 2-phenoxyacetic acid (122-59-8) → benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182268-38-8)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1039/cc9960001989

Reference yield: 51.0%

Phenoxyacetyl chloride (701-99-5) + (S)-3-Methyl-7-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester → benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182268-38-8) + benzyl (-)-(6S,7S)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182268-29-7)

Guidance literature:

In dichloromethane; at 20 ℃; for 20h;

DOI:10.1016/S0040-4020(00)00486-5

Reference yield:

6-Aminopenicillanic Acid (551-16-6) → benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182268-38-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 49 percent / Na₂CO₃ / H₂O / 2 h / 20 °C

2.1: 71 percent / triethylamine / dimethylformamide / 6 h / 20 °C

3.1: Cl₂ / CH₂Cl₂; CCl₄ / 20 °C

4.1: 2.22 g / SnCl₂ / tetrahydrofuran / 2 h / 20 °C

5.1: 85 percent / m-chloroperbenzoic acid / CHCl₃ / 1.5 h / 0 °C

6.1: 33 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 100 °C

7.1: 39 percent / N₂H₄*H₂O / dimethylformamide / 0.5 h / -15 °C

8.1: 83 percent / MgSO₄ / CH₂Cl₂ / 10 h / 20 °C

9.1: PhLi; DMF / tetrahydrofuran; cyclohexane; diethyl ether / -78 °C

9.2: 253 mg / H₂₀; AcOH

10.1: 20 percent / CH₂Cl₂ / 20 h / 20 °C

With chlorine; sodium carbonate; magnesium sulfate; toluene-4-sulfonic acid; hydrazine hydrate; phenyllithium; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; tin(ll) chloride; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; chloroform; cyclohexane; water; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Esterification / 3.1: Chlorination / 4.1: Cyclization / 5.1: Oxidation / 6.1: Rearrangement / 7.1: Substitution / 8.1: Condensation / 9.1: Metallation / 9.2: Hydrolysis / 10.1: Acylation;

DOI:10.1016/S0040-4020(00)00486-5

upstream raw materials:

benzyl (-)-(6S,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2-phenoxyacetic acid

Phenoxyacetyl chloride

6-Aminopenicillanic Acid

Downstream raw materials:

(-)-(6S,7R)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid