5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid methyl ester

Base Information

• Chemical Name: 5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid methyl ester
• CAS No.: 235793-02-9
• Molecular Formula: C₂₆H₂₇N₃O₆
• Molecular Weight: 477.517

Synonyms:5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid methyl ester

Chemical Property of 5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid methyl ester

There total 7 articles about 5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid 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:

4-phenyl-1-piperazine (92-54-6) → 5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid methyl ester (235793-02-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / DMAP, Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 90 percent / I₂, NaHCO₃, H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 85 percent / Et₃N / 2(PPh₃)2>, CuI / tetrahydrofuran / 18 h / Ambient temperature

4: 98 percent / MnO₂ / CH₂Cl₂ / 6 h / Ambient temperature

5: 1.) NaHMDS / 1.) DMF, 0 to r.t., 1 h, 2.) DMF, THF, r.t., 8 h

6: DMAP / tetrahydrofuran / 2 h / Ambient temperature

7: EDC / tetrahydrofuran / 4 h / Ambient temperature

With dmap; manganese(IV) oxide; water; iodine; sodium hexamethyldisilazane; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(SICI)1521-3773(19980216)37:3<325::AID-ANIE325>3.0.CO;2-L

Reference yield:

tert-butyl 4-(4-iodophenyl)tetrahydro-1(2H)-pyrazinecarboxylate (151978-66-4) → 5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid methyl ester (235793-02-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / Et₃N / 2(PPh₃)2>, CuI / tetrahydrofuran / 18 h / Ambient temperature

2: 98 percent / MnO₂ / CH₂Cl₂ / 6 h / Ambient temperature

3: 1.) NaHMDS / 1.) DMF, 0 to r.t., 1 h, 2.) DMF, THF, r.t., 8 h

4: DMAP / tetrahydrofuran / 2 h / Ambient temperature

5: EDC / tetrahydrofuran / 4 h / Ambient temperature

With dmap; manganese(IV) oxide; sodium hexamethyldisilazane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(SICI)1521-3773(19980216)37:3<325::AID-ANIE325>3.0.CO;2-L

Reference yield:

4-phenyl-piperazine-1-carboxylic acid tert-butyl ester (77278-63-8) → 5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid methyl ester (235793-02-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / I₂, NaHCO₃, H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 85 percent / Et₃N / 2(PPh₃)2>, CuI / tetrahydrofuran / 18 h / Ambient temperature

3: 98 percent / MnO₂ / CH₂Cl₂ / 6 h / Ambient temperature

4: 1.) NaHMDS / 1.) DMF, 0 to r.t., 1 h, 2.) DMF, THF, r.t., 8 h

5: DMAP / tetrahydrofuran / 2 h / Ambient temperature

6: EDC / tetrahydrofuran / 4 h / Ambient temperature

With dmap; manganese(IV) oxide; water; iodine; sodium hexamethyldisilazane; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(SICI)1521-3773(19980216)37:3<325::AID-ANIE325>3.0.CO;2-L

upstream raw materials:

methanol

4-phenyl-1-piperazine

4-phenyl-piperazine-1-carboxylic acid tert-butyl ester

tert-butyl 4-(4-iodophenyl)tetrahydro-1(2H)-pyrazinecarboxylate

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