tert-butyl 4-(isobutylamino)carbonyl-2'-{[3-(methoxycarbonyl)phenyl]amino}carbonyl-4'-[methyl(trifluoroacetyl)amino]biphenyl-2-carboxylate

Base Information

• Chemical Name: tert-butyl 4-(isobutylamino)carbonyl-2'-{[3-(methoxycarbonyl)phenyl]amino}carbonyl-4'-[methyl(trifluoroacetyl)amino]biphenyl-2-carboxylate
• CAS No.: 790230-15-8
• Molecular Formula: C₃₄H₃₆F₃N₃O₇
• Molecular Weight: 655.671
• Mol file: 790230-15-8.mol

Synonyms:

Chemical Property of tert-butyl 4-(isobutylamino)carbonyl-2'-{[3-(methoxycarbonyl)phenyl]amino}carbonyl-4'-[methyl(trifluoroacetyl)amino]biphenyl-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-(isobutylamino)carbonyl-2'-{[3-(methoxycarbonyl)phenyl]amino}carbonyl-4'-[methyl(trifluoroacetyl)amino]biphenyl-2-carboxylate

There total 15 articles about tert-butyl 4-(isobutylamino)carbonyl-2'-{[3-(methoxycarbonyl)phenyl]amino}carbonyl-4'-[methyl(trifluoroacetyl)amino]biphenyl-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:

4-bromo-3-(hydroxymethyl)benzoic acid (790230-04-5) → tert-butyl 4-(isobutylamino)carbonyl-2'-{[3-(methoxycarbonyl)phenyl]amino}carbonyl-4'-[methyl(trifluoroacetyl)amino]biphenyl-2-carboxylate (790230-15-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 4.27 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 20 °C

2.1: MnO₂ / CHCl₃ / 1 h / 70 °C

3.1: 3.53 g / 4-methylbenzenesulfonic acid monohydrate / toluene / 12 h / Heating

4.1: n-butyl lithium / tetrahydrofuran; hexane / 2 h / -78 °C

4.2: triisopropyl borate / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

4.3: 280 mg / hydrochloric acid / tetrahydrofuran; hexane; H₂O / 3 h / 20 °C

5.1: K₃PO₄ / Pd(PPh₃)4 / dimethylformamide / 24 h / 120 °C

6.1: NaH₂PO₄*2H₂O; 2-methyl-2-butene; sodium chlorite / 2-methyl-propan-2-ol; H₂O; acetonitrile / 12 h / 20 °C

7.1: 2.15 g / MgSO₄; H₂SO₄ / CH₂Cl₂

8.1: 1.23 g / NaOH / methanol; H₂O / 2 h / Heating

9.1: 1.28 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 80 °C

10.1: 1.00 g / hydrogen / Pd/C / methanol / 12 h / 20 °C

11.1: pyridine / CH₂Cl₂ / 72 h / 20 °C

12.1: 190 mg / K₂CO₃ / butan-2-one / 4 h / 40 °C

With pyridine; manganese(IV) oxide; sodium hydroxide; sodium chlorite; potassium phosphate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; sulfuric acid; p-toluenesulfonic acid monohydrate; hydrogen; magnesium sulfate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile; butanone; tert-butyl alcohol; 5.1: Suzuki coupling;

DOI:10.1016/j.bmc.2006.08.010

Reference yield:

4-bromo-3-formyl-N-isobutyl-benzamide → tert-butyl 4-(isobutylamino)carbonyl-2'-{[3-(methoxycarbonyl)phenyl]amino}carbonyl-4'-[methyl(trifluoroacetyl)amino]biphenyl-2-carboxylate (790230-15-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 3.53 g / 4-methylbenzenesulfonic acid monohydrate / toluene / 12 h / Heating

2.1: n-butyl lithium / tetrahydrofuran; hexane / 2 h / -78 °C

2.2: triisopropyl borate / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

2.3: 280 mg / hydrochloric acid / tetrahydrofuran; hexane; H₂O / 3 h / 20 °C

3.1: K₃PO₄ / Pd(PPh₃)4 / dimethylformamide / 24 h / 120 °C

4.1: NaH₂PO₄*2H₂O; 2-methyl-2-butene; sodium chlorite / 2-methyl-propan-2-ol; H₂O; acetonitrile / 12 h / 20 °C

5.1: 2.15 g / MgSO₄; H₂SO₄ / CH₂Cl₂

6.1: 1.23 g / NaOH / methanol; H₂O / 2 h / Heating

7.1: 1.28 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 80 °C

8.1: 1.00 g / hydrogen / Pd/C / methanol / 12 h / 20 °C

9.1: pyridine / CH₂Cl₂ / 72 h / 20 °C

10.1: 190 mg / K₂CO₃ / butan-2-one / 4 h / 40 °C

With pyridine; sodium hydroxide; sodium chlorite; potassium phosphate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; sulfuric acid; p-toluenesulfonic acid monohydrate; hydrogen; magnesium sulfate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; butanone; tert-butyl alcohol; 3.1: Suzuki coupling;

DOI:10.1016/j.bmc.2006.08.010

Reference yield:

methyl 3-(acetyloxy)methyl-4-bromobenzoate (254746-41-3) → tert-butyl 4-(isobutylamino)carbonyl-2'-{[3-(methoxycarbonyl)phenyl]amino}carbonyl-4'-[methyl(trifluoroacetyl)amino]biphenyl-2-carboxylate (790230-15-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 8.29 g / NaOH / methanol; H₂O / 2 h / 20 °C

2.1: 4.27 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 20 °C

3.1: MnO₂ / CHCl₃ / 1 h / 70 °C

4.1: 3.53 g / 4-methylbenzenesulfonic acid monohydrate / toluene / 12 h / Heating

5.1: n-butyl lithium / tetrahydrofuran; hexane / 2 h / -78 °C

5.2: triisopropyl borate / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

5.3: 280 mg / hydrochloric acid / tetrahydrofuran; hexane; H₂O / 3 h / 20 °C

6.1: K₃PO₄ / Pd(PPh₃)4 / dimethylformamide / 24 h / 120 °C

7.1: NaH₂PO₄*2H₂O; 2-methyl-2-butene; sodium chlorite / 2-methyl-propan-2-ol; H₂O; acetonitrile / 12 h / 20 °C

8.1: 2.15 g / MgSO₄; H₂SO₄ / CH₂Cl₂

9.1: 1.23 g / NaOH / methanol; H₂O / 2 h / Heating

10.1: 1.28 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 80 °C

11.1: 1.00 g / hydrogen / Pd/C / methanol / 12 h / 20 °C

12.1: pyridine / CH₂Cl₂ / 72 h / 20 °C

13.1: 190 mg / K₂CO₃ / butan-2-one / 4 h / 40 °C

With pyridine; manganese(IV) oxide; sodium hydroxide; sodium chlorite; potassium phosphate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; sulfuric acid; p-toluenesulfonic acid monohydrate; hydrogen; magnesium sulfate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile; butanone; tert-butyl alcohol; 6.1: Suzuki coupling;

DOI:10.1016/j.bmc.2006.08.010

upstream raw materials:

methyl iodide

4-bromo-3-(hydroxymethyl)benzoic acid

methyl 3-(acetyloxy)methyl-4-bromobenzoate

4-bromo-3-hydroxymethyl-N-isobutylbenzamide

Downstream raw materials:

tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate

2'-(3-carboxy-phenylcarbamoyl)-4-isobutylcarbamoyl-4'-methylamino-biphenyl-2-carboxylic acid tert-butyl ester