4-Nitrobenzyl 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Base Information

• Chemical Name: 4-Nitrobenzyl 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS No.: 85769-20-6
• Molecular Formula: C₁₉H₁₄N₂O₆S
• Molecular Weight: 398.396

Synonyms:4-Nitrobenzyl 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Chemical Property of 4-Nitrobenzyl 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Chemical Property:

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Technology Process of 4-Nitrobenzyl 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

There total 8 articles about 4-Nitrobenzyl 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-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: 18.0%

4-nitrobenzyl 2-(4-allylsulphinylazetidin-2-on-1-yl)-3-phenoxy-3-thioxopropionate (85769-19-3) → 4-Nitrobenzyl 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (85769-20-6)

Guidance literature:

With triphenylphosphine; In 1,4-dioxane; at 100 ℃; for 0.25h;

DOI:10.1016/S0040-4039(00)86273-5

Reference yield: 11.0%

1,4-dioxane (123-91-1,28347-88-8,28347-91-3,39449-24-6,54841-74-6) + 4-nitrobenzyl 2-(4-allylsulphinylazetidin-2-on-1-yl)-3-phenoxy-3-thioxopropionate (85769-19-3) → 4-Nitrobenzyl 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (85769-20-6)

Guidance literature:

With triphenylphosphine; Trimethylacetic acid; In ethyl acetate;

Reference yield:

4'-Nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)acetate (83362-25-8) → 4-Nitrobenzyl 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (85769-20-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) LiN(SiMe₃)2 / 1.) THF, -78 deg C

2: neat (no solvent) / 0 - 20 °C

3: m-chloroperbenzoic acid / ethyl acetate / -20 °C

4: 90 percent / imidazole / dioxane; H₂O / 5 °C

5: 18 percent / triphenylphosphine / dioxane / 0.25 h / 100 °C

With 1H-imidazole; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; In 1,4-dioxane; water; ethyl acetate;

DOI:10.1016/S0040-4039(00)86273-5

upstream raw materials:

4-nitrobenzyl 2-(4-allylsulphinylazetidin-2-on-1-yl)-3-phenoxy-3-thioxopropionate

4'-Nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)acetate

(2-Allylsulfanyl-4-oxo-azetidin-1-yl)-phenoxythiocarbonyl-acetic acid 4-nitro-benzyl ester

(E)-2-(2-Allylsulfanyl-4-oxo-azetidin-1-yl)-3-(2,2-dimethyl-propionylsulfanyl)-3-phenoxy-acrylic acid 4-nitro-benzyl ester

Downstream raw materials:

sodium 7-oxo-3-phenoxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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