Diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate

Base Information

• Chemical Name: Diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate
• CAS No.: 86694-79-3
• Molecular Formula: C16H19NO5
• Molecular Weight: 305.331
• DSSTox Substance ID: DTXSID10542502
• Nikkaji Number: J2.609.213B
• Wikidata: Q82419197
• Mol file: 86694-79-3.mol

Synonyms:86694-79-3;Diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate;SCHEMBL11064509;DTXSID10542502;RQAHYNAQWHFDIS-UHFFFAOYSA-N;Diethyl 1-benzyl-4-oxo-2,2-azetidine-dicarboxylate

Chemical Property of Diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 305.12632271
• Heavy Atom Count: 22
• Complexity: 424

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CC(=O)N1CC2=CC=CC=C2)C(=O)OCC

Technology Process of Diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate

There total 3 articles about Diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate 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%

diethyl 2-(N-benzyl-2-bromoacetamido)malonate (1071913-15-9) → diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate (86694-79-3)

Guidance literature:

With 1-butyl-3-methylimidazolium Tetrafluoroborate; at 45 ℃; Electrolysis; Inert atmosphere;

diethyl 2-(N-benzyl-2-bromoacetamido)malonate; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/adsc.200800049

Reference yield: 75.0%

diethyl N-benzyl-N-(chloroacetyl)aminomalonate (86694-78-2) → diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate (86694-79-3)

Guidance literature:

With triethylamine; In benzene; for 8h; Ambient temperature;

Reference yield:

diethyl 2-(benzylamino)malonate hydrochloride (56598-99-3) → diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate (86694-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / benzene / 1 h / Heating

2: 75 percent / triethylamine / benzene / 8 h / Ambient temperature

With triethylamine; In benzene;

upstream raw materials:

diethyl N-benzyl-N-(chloroacetyl)aminomalonate

diethyl 2-(benzylamino)malonate hydrochloride

diethyl 2-(N-benzyl-2-bromoacetamido)malonate

Downstream raw materials:

1-benzyl-4-(mesyloxymethyl)-2-azetidinone

1-Benzyl-4-(hydroxymethyl)azetidin-2-one

ethyl 4-oxo-1-(phenylmethyl)-2-azetidinecarboxylate