(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl ester

Base Information

• Chemical Name: (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl ester
• CAS No.: 83290-69-1
• Molecular Formula: C₂₃H₂₁ClN₂O₃S
• Molecular Weight: 440.95
• Mol file: 83290-69-1.mol

Synonyms:

Chemical Property of (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl ester

There total 4 articles about (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl 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: 9.0%

(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzyl ester (86832-59-9) → (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl ester (83290-69-1) + (R)-2-[(1R,5R)-3-(Chloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-3-methyl-but-3-enoic acid benzyl ester (80405-24-9) + (R)-3-Chloromethyl-2-[(1R,5R)-3-(chloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-but-3-enoic acid benzyl ester (80405-30-7) + (R)-2-[(1R,5R)-3-(Dichloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-3-methyl-but-3-enoic acid benzyl ester (80405-20-5)

Guidance literature:

With sulfuric acid; sodium chloride; In chloroform; water; Ambient temperature; electrolysis with Pt electrodes at a constant current (10 mA/cm²), lower Cl(-) concentration;

DOI:10.1002/bscb.19820911202

Reference yield:

(R)-3-Chloromethyl-2-[(1R,5R)-3-(dichloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-but-3-enoic acid benzyl ester (86832-60-2) → (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl ester (83290-69-1)

Guidance literature:

With acetic acid; zinc; In dichloromethane; at 0 - 2 ℃; Yield given;

DOI:10.1002/bscb.19820911202

Reference yield:

(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzyl ester (86832-59-9) → (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl ester (83290-69-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 9 percent / NaCl, H₂SO₄ / H₂O; CHCl₃ / Ambient temperature; electrolysis with Pt electrodes at a constant current (10 mA/cm²), lower Cl(-) concentration

2: 85 percent / NaCl, H₂SO₄ / H₂O; CHCl₃ / Ambient temperature; electrolysis with Pt electrodes at a constant current (10 mA/cm²)

3: zinc dust, AcOH / CH₂Cl₂ / 0 - 2 °C

With sulfuric acid; acetic acid; sodium chloride; zinc; In dichloromethane; chloroform; water;

DOI:10.1002/bscb.19820911202

upstream raw materials:

(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzyl ester

(R)-3-Chloromethyl-2-[(1R,5R)-3-(dichloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-but-3-enoic acid benzyl ester

(R)-2-[(1R,5R)-3-(Dichloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-3-methyl-but-3-enoic acid benzyl ester

Downstream raw materials:

(R)-3-Chloromethyl-2-((3R,4R)-2-oxo-4-pentachlorophenyldisulfanyl-3-phenylacetylamino-azetidin-1-yl)-but-3-enoic acid benzyl ester

(R)-2-{(1R,5R)-3-[(Benzothiazol-2-ylsulfanyl)-phenyl-methyl]-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-3-chloromethyl-but-3-enoic acid benzyl ester

(R)-2-{(1R,5R)-3-[Bis-(benzothiazol-2-ylsulfanyl)-phenyl-methyl]-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-3-chloromethyl-but-3-enoic acid benzyl ester

(R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl ester