Benzyl 2-[2-(methylsulfanyl)-4-oxoazetidin-1-yl]benzoate

Base Information

• Chemical Name: Benzyl 2-[2-(methylsulfanyl)-4-oxoazetidin-1-yl]benzoate
• CAS No.: 90136-87-1
• Molecular Formula: C18H17NO3S
• Molecular Weight: 327.404
• DSSTox Substance ID: DTXSID00522570
• Mol file: 90136-87-1.mol

Synonyms:90136-87-1;Benzyl 2-[2-(methylsulfanyl)-4-oxoazetidin-1-yl]benzoate;DTXSID00522570

Chemical Property of Benzyl 2-[2-(methylsulfanyl)-4-oxoazetidin-1-yl]benzoate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 327.09291458
• Heavy Atom Count: 23
• Complexity: 436

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1CC(=O)N1C2=CC=CC=C2C(=O)OCC3=CC=CC=C3

Technology Process of Benzyl 2-[2-(methylsulfanyl)-4-oxoazetidin-1-yl]benzoate

There total 5 articles about Benzyl 2-[2-(methylsulfanyl)-4-oxoazetidin-1-yl]benzoate 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: 87.0%

(3R,4S/3S,4R)-1-(2-Benzyloxycarbonylphenyl)-3-chlor-4-methylthio-2-azetidinon → 1-(2-Benzyloxycarbonylphenyl)-4-methylthio-2-azetidinon (90136-87-1)

Guidance literature:

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In benzene; for 2h; Heating;

DOI:10.1007/BF00798412

Reference yield:

benzyl anthranilate (82185-41-9) → 1-(2-Benzyloxycarbonylphenyl)-4-methylthio-2-azetidinon (90136-87-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) POCl₃; 2.) 2 N NaOH / 1.) benzene, 16 h, RT; 2.) water

2: 68 percent / H₂S / dimethylformamide / 1.5 h / -5 °C

3: anhydrous K₂CO₃ / acetone / 20 h / 20 °C

4: 61 percent / NEt₃ / benzene / 5 h / Heating

5: 87 percent / Bu3SnH; α,α'-azoisobutyronitrile / benzene / 2 h / Heating

With sodium hydroxide; azobisisobutyronitrile; hydrogen sulfide; tri-n-butyl-tin hydride; potassium carbonate; triethylamine; trichlorophosphate; In N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1007/BF00798412

Reference yield:

N-Thioformylanthranilsaeurebenzylester (90136-84-8) → 1-(2-Benzyloxycarbonylphenyl)-4-methylthio-2-azetidinon (90136-87-1)

Guidance literature:

Multi-step reaction with 3 steps

1: anhydrous K₂CO₃ / acetone / 20 h / 20 °C

2: 61 percent / NEt₃ / benzene / 5 h / Heating

3: 87 percent / Bu3SnH; α,α'-azoisobutyronitrile / benzene / 2 h / Heating

With azobisisobutyronitrile; tri-n-butyl-tin hydride; potassium carbonate; triethylamine; In acetone; benzene;

DOI:10.1007/BF00798412

upstream raw materials:

benzyl anthranilate

N-Thioformylanthranilsaeurebenzylester

2-Methylsulfanylmethyleneamino-benzoic acid benzyl ester

N¹-(2-Benzyloxycarbonylphenyl)-N²-dimethylformamidin

Downstream raw materials:

1-(2-Carboxyphenyl)-4-methylthio-2-azetidinon