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

Base Information

• Chemical Name: (6S,7S)-benzyl 7-(1,3-dioxoisoindolin-2-yl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 182186-35-2
• Molecular Formula: C₂₃H₁₈N₂O₅S
• Molecular Weight: 434.472
• Mol file: 182186-35-2.mol

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

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

There total 13 articles about (6S,7S)-benzyl 7-(1,3-dioxoisoindolin-2-yl)-3-methyl-8-oxo-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: 57.0%

(R)-2-[(2S,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxysulfanyl-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester (214344-42-0) → (6S,7S)-benzyl 7-(1,3-dioxoisoindolin-2-yl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182186-35-2)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 100 ℃; for 1h;

DOI:10.1016/S0040-4039(98)01482-8

Reference yield: 52.0%

benzyl (-)-(2S,4S,5S,6S)-3,3-dimethyl-7-oxo-6-phthalimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide (182268-27-5) → (6S,7S)-benzyl 7-(1,3-dioxoisoindolin-2-yl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182186-35-2)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; at 100 ℃; for 2h;

Reference yield:

6-Aminopenicillanic Acid (551-16-6) → (6S,7S)-benzyl 7-(1,3-dioxoisoindolin-2-yl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182186-35-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 49 percent / Na₂CO₃ / H₂O / 2 h / 20 °C

2: 71 percent / triethylamine / dimethylformamide / 6 h / 20 °C

3: 98 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1.5 h / 20 °C

4: Cl₂ / CH₂Cl₂; CCl₄ / 0.5 h / 20 °C

5: 470 mg / SnCl₂ / tetrahydrofuran / 2 h / 20 °C

6: 265 mg / ozone / acetone / cooling

7: 50 percent / p-toluenesulfonic acid / dimethylformamide / 1.5 h / 100 °C

With chlorine; sodium carbonate; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tin(ll) chloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1: Substitution / 2: Esterification / 3: epimerisation / 4: Chlorination / 5: Cyclization / 6: Oxidation / 7: Rearrangement;

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

upstream raw materials:

benzyl (-)-(2S,4S,5S,6S)-3,3-dimethyl-7-oxo-6-phthalimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide

(R)-2-[(2S,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxysulfanyl-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

(2S,5R,6R)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

6-Aminopenicillanic Acid

Downstream raw materials:

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

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

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