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

Base Information

• Chemical Name: {4-[{1-[4-benzoyl-2-(3-bromo-propoxy)-phenyl]-ethyl}-(4-chloro-benzenesulfonyl)-amino]-2,5-difluoro-phenoxy}-acetic acid
• CAS No.: 920012-38-0
• Molecular Formula: C₃₂H₂₇BrClF₂NO₇S
• Molecular Weight: 722.989

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

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

Chemical Property:

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

There total 16 articles about {4-[{1-[4-benzoyl-2-(3-bromo-propoxy)-phenyl]-ethyl}-(4-chloro-benzenesulfonyl)-amino]-2,5-difluoro-phenoxy}-acetic acid 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-[{1-[4-benzoyl-2-(3-bromo-propoxy)-phenyl]-ethyl}-(4-chloro-benzenesulfonyl)-amino]-2,5-difluoro-phenoxy}-acetic acid allyl ester (909124-82-9) → {4-[{1-[4-benzoyl-2-(3-bromo-propoxy)-phenyl]-ethyl}-(4-chloro-benzenesulfonyl)-amino]-2,5-difluoro-phenoxy}-acetic acid (920012-38-0)

Guidance literature:

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmcl.2006.05.091

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 (920012-38-0)

Guidance literature:

Multi-step reaction with 7 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

7: Pd(PPh₃)4; pyrrolidine / tetrahydrofuran / 20 °C

With pyrrolidine; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 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 (920012-38-0)

Guidance literature:

Multi-step reaction with 7 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

7: Pd(PPh₃)4; pyrrolidine / tetrahydrofuran / 20 °C

With pyrrolidine; pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 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

upstream raw materials:

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

2.5-difluoro-4-nitrophenol

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

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

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