Acetic acid, [4-[[1-[4-benzoyl-2-(3-bromopropoxy)phenyl]ethyl][(4-chlorophenyl)sulfon yl]amino]-2,5-difluorophenoxy]-, 2-propenyl ester

Base Information

• Chemical Name: Acetic acid, [4-[[1-[4-benzoyl-2-(3-bromopropoxy)phenyl]ethyl][(4-chlorophenyl)sulfon yl]amino]-2,5-difluorophenoxy]-, 2-propenyl ester
• CAS No.: 909124-82-9
• Molecular Formula: C₃₅H₃₁BrClF₂NO₇S
• Molecular Weight: 763.053

Synonyms:

Chemical Property of Acetic acid, [4-[[1-[4-benzoyl-2-(3-bromopropoxy)phenyl]ethyl][(4-chlorophenyl)sulfon yl]amino]-2,5-difluorophenoxy]-, 2-propenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid, [4-[[1-[4-benzoyl-2-(3-bromopropoxy)phenyl]ethyl][(4-chlorophenyl)sulfon yl]amino]-2,5-difluorophenoxy]-, 2-propenyl ester

There total 13 articles about Acetic acid, [4-[[1-[4-benzoyl-2-(3-bromopropoxy)phenyl]ethyl][(4-chlorophenyl)sulfon yl]amino]-2,5-difluorophenoxy]-, 2-propenyl 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:

3-hydroxy-4-iodo-N-methoxy-N-methyl-benzamide (909124-64-7) → {4-[{1-[4-benzoyl-2-(3-bromo-propoxy)-phenyl]-ethyl}-(4-chloro-benzenesulfonyl)-amino]-2,5-difluoro-phenoxy}-acetic acid allyl ester (909124-82-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / PdCl₂(PPh₃)2; PPh₃; CuI / Et₃N / tetrahydrofuran / 20 °C

2: 89 percent / PPh₃; DEAD / toluene / 0 - 20 °C

3: 70 percent / formic acid / 60 °C

4: 97 percent / NaBH₄ / methanol / 0 °C

5: 98 percent / tetrahydrofuran / -78 - 20 °C

6: 81 percent / PPh₃; DEAD / toluene / 0 - 20 °C

With bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; copper(l) iodide; formic acid; triphenylphosphine; diethylazodicarboxylate; triethylamine; In tetrahydrofuran; methanol; toluene; 1: Sonogashira coupling / 2: Mitsunobu reaction / 6: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2006.05.091

Reference yield:

2.5-difluoro-4-nitrophenol (120103-18-6) → {4-[{1-[4-benzoyl-2-(3-bromo-propoxy)-phenyl]-ethyl}-(4-chloro-benzenesulfonyl)-amino]-2,5-difluoro-phenoxy}-acetic acid allyl ester (909124-82-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / K₂CO₃ / dimethylformamide / 20 °C

2: H₂ / Pd/C / methanol / 20 °C

3: 86 percent / pyridine / CH₂Cl₂ / 20 °C

4: TFA / CH₂Cl₂ / 0 - 20 °C

5: 85 percent / EDCI*HCl; HOBt*H₂O; Et₃N / dimethylformamide; tetrahydrofuran / 20 °C

6: 81 percent / PPh₃; DEAD / toluene / 0 - 20 °C

With pyridine; hydrogen; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 6: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2006.05.091

Reference yield:

3-hydroxy-N-methoxy-N-methyl-4-nitro-benzamide (909124-60-3) → {4-[{1-[4-benzoyl-2-(3-bromo-propoxy)-phenyl]-ethyl}-(4-chloro-benzenesulfonyl)-amino]-2,5-difluoro-phenoxy}-acetic acid allyl ester (909124-82-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / H₂ / Pd/C / methanol / 20 °C

2.1: NaNO₂; aq. HCl / 0 °C

2.2: 68 percent / KI / 20 °C

3.1: 98 percent / PdCl₂(PPh₃)2; PPh₃; CuI / Et₃N / tetrahydrofuran / 20 °C

4.1: 89 percent / PPh₃; DEAD / toluene / 0 - 20 °C

5.1: 70 percent / formic acid / 60 °C

6.1: 97 percent / NaBH₄ / methanol / 0 °C

7.1: 98 percent / tetrahydrofuran / -78 - 20 °C

8.1: 81 percent / PPh₃; DEAD / toluene / 0 - 20 °C

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; copper(l) iodide; formic acid; hydrogen; triphenylphosphine; sodium nitrite; diethylazodicarboxylate; palladium on activated charcoal; triethylamine; In tetrahydrofuran; methanol; toluene; 3.1: Sonogashira coupling / 4.1: Mitsunobu reaction / 8.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2006.05.091

upstream raw materials:

2.5-difluoro-4-nitrophenol

3-hydroxy-4-iodo-N-methoxy-N-methyl-benzamide

4-amino-3-hydroxy-N-methoxy-N-methyl-benzamide

3-hydroxy-N-methoxy-N-methyl-4-nitro-benzamide

Downstream raw materials:

{4-[{1-[4-benzoyl-2-(3-bromo-propoxy)-phenyl]-ethyl}-(4-chloro-benzenesulfonyl)-amino]-2,5-difluoro-phenoxy}-acetic acid pentafluorophenyl ester

{4-[{1-[4-benzoyl-2-(3-bromo-propoxy)-phenyl]-ethyl}-(4-chloro-benzenesulfonyl)-amino]-2,5-difluoro-phenoxy}-acetic acid

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