trans(+/-)-3-ethyl-4,β-dioxo-2-azetidinbutanoic acid, (4-nitrophenyl)methyl ester

Base Information

• Chemical Name: trans(+/-)-3-ethyl-4,β-dioxo-2-azetidinbutanoic acid, (4-nitrophenyl)methyl ester
• CAS No.: 83997-54-0
• Molecular Formula: C₁₆H₁₈N₂O₆
• Molecular Weight: 334.329
• Mol file: 83997-54-0.mol

Synonyms:trans(+/-)-3-ethyl-4,β-dioxo-2-azetidinbutanoic acid, (4-nitrophenyl)methyl ester

Chemical Property of trans(+/-)-3-ethyl-4,β-dioxo-2-azetidinbutanoic acid, (4-nitrophenyl)methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans(+/-)-3-ethyl-4,β-dioxo-2-azetidinbutanoic acid, (4-nitrophenyl)methyl ester

There total 21 articles about trans(+/-)-3-ethyl-4,β-dioxo-2-azetidinbutanoic acid, (4-nitrophenyl)methyl 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: 66.0%

magnesium 4-nitrobenzyl malonate (105995-50-4) + (3S,4S)-3-Ethyl-4-(2-imidazol-1-yl-2-oxo-ethyl)-azetidin-2-one → 3-ethyl-4-(2-oxo-3-p-nitrobenzyloxycarbonylpropyl)azetidin-2-one (79252-33-8,83997-54-0,84621-80-7,84621-84-1,84680-15-9)

Guidance literature:

In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1039/P19810002228

Reference yield:

Acetic acid (Z)-2-(3-ethyl-4-oxo-azetidin-2-yl)-vinyl ester (83934-90-1,83997-51-7,83997-52-8,83997-53-9) → trans(+/-)-3-ethyl-4,β-dioxo-2-azetidinbutanoic acid, (4-nitrophenyl)methyl ester (83997-54-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / Pd/C / ethyl acetate / Ambient temperature

2: 85 percent / K₂CO₃ / methanol / Ambient temperature

3: TsOH / toluene / 18 h / Ambient temperature

4: 1N potassium ter-amylate

5: 10percent AcOH / 3 h / 70 °C

6: KMnO₄ / H₂O / Ambient temperature

7: 1.) N,N'-carbonyldiimidazole / 1.) THF, r.t., 2 h 2.)THF, r.t. 19 h

With potassium permanganate; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In methanol; water; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(00)87545-0

Reference yield:

diethyl (+/-)-3-ethyl-1-(2,4-dimethoxybenzyl)-4-oxo-2,2-azetidinedicarboxylate (91922-04-2) → 3-ethyl-4-(2-oxo-3-p-nitrobenzyloxycarbonylpropyl)azetidin-2-one (79252-33-8,83997-54-0,84621-80-7,84621-84-1,84680-15-9)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂O, NaCl / dimethylsulfoxide / 9 h / 180 °C

2: aq. NaOH / ethanol / 0.25 h / 0 °C

3: 1.) ethyl chloroformate, triethylamine / 1.) THF, 20 min, -15 deg C, 2.) ether, 2 h, RT

4: 51 percent / tetrahydrofuran; H₂O / 4 h / Irradiation

5: CH₂Cl₂ / Ambient temperature

6: K₂S₂O₈, Na₂HPO₄*2H₂O / acetonitrile; H₂O / 4 h / Heating

7: 74 percent / H₂ / Pd-C / ethanol

8: 1.) 1,1'-carbonyldiimidazole / 1.) CH₃CN, 30 min, RT, 2.) 12 h

With sodium hydroxide; disodium hydrogenphosphate; dipotassium peroxodisulfate; water; hydrogen; chloroformic acid ethyl ester; triethylamine; 1,1'-carbonyldiimidazole; sodium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

upstream raw materials:

magnesium salt of mono p-nitro-benzylester of malonic acid

(+)-trans-4-carboxymethyl-3-ethylazetidin-2-one

4-[2-(acetyloxy)ethyl]-3-ethyl-2-azetidinone

3-ethyl-4-[2-(hydroxy)ethyl]-2-azetidinone

Downstream raw materials:

PS-5

(5R,6R)-6-Ethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-phenyl ester

(3R,4R)-3-ethyl-4-<3-diazo-2-oxo-3-<<(p-nitrobenzyl)oxy>carbonyl>propyl>-2-azetidinone