5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid

Base Information

• Chemical Name: 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid
• CAS No.: 1404378-09-1
• Molecular Formula: C₂₈H₃₇ClN₂O₄
• Molecular Weight: 501.066
• Mol file: 1404378-09-1.mol

Synonyms:5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid

Chemical Property of 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid

There total 26 articles about 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric 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:

methyl 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valerate → 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid (1404378-09-1)

Guidance literature:

With hydrogen bromide; acetic acid; In water; at 20 - 60 ℃;

Reference yield:

4,4-dimethylpentanoic acid (1118-47-4) → 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid (1404378-09-1)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water / 20 °C / Cooling with ice

2.1: 1,1,3,3-Tetramethyldisiloxane / (Ph₃P)2IrCl(CO) / toluene / 3 h / 20 °C

3.1: hydroquinone / acetonitrile / 90 °C

4.1: methyl p-toluene sulfonate / 2 h / 105 °C

5.1: hydrogen / rhodium contaminated with carbon / tetrahydrofuran / 35 h / 20 °C

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C

7.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C

7.2: Cooling with ice

8.1: triphenylphosphine / dichloromethane / 0.75 h / Cooling with ice

8.2: 1 h / Cooling with ice

8.3: Cooling with ice

9.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

9.2: 0.33 h / Cooling with ice

10.1: pyridine / methanol / 20 °C

11.1: Iodine monochloride / dichloromethane / 1 h / Cooling with ice

12.1: potassium phosphate / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 1 h / 80 °C / Inert atmosphere

13.1: hydrogen / palladium on activated charcoal / tetrahydrofuran; methanol / 5 h / 20 °C / 760.05 Torr

14.1: sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 2 h / 20 °C

15.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C

16.1: trifluoroacetic acid / chloroform / 20 °C / Cooling with ice

17.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water / 20 - 70 °C

18.1: hydrogen bromide; acetic acid / water / 20 - 60 °C

With pyridine; sodium hypochlorite; sodium chlorite; potassium phosphate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,1,3,3-Tetramethyldisiloxane; hydrogen bromide; hydrogen; Iodine monochloride; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; hydroquinone; methyl p-toluene sulfonate; triphenylphosphine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; rhodium contaminated with carbon; (Ph₃P)2IrCl(CO); In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

pivalaldehyde (630-19-3) → 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid (1404378-09-1)

Guidance literature:

Multi-step reaction with 20 steps

1.1: sodium ethanolate / ethanol / 1.5 h / Cooling with ice

1.2: 3.5 h / 20 °C

2.1: hydrogen / palladium 10% on activated carbon / ethanol; tetrahydrofuran; methanol / 10.5 h / 20 °C / 760.05 Torr

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water / 20 °C / Cooling with ice

4.1: 1,1,3,3-Tetramethyldisiloxane / (Ph₃P)2IrCl(CO) / toluene / 3 h / 20 °C

5.1: hydroquinone / acetonitrile / 90 °C

6.1: methyl p-toluene sulfonate / 2 h / 105 °C

7.1: hydrogen / rhodium contaminated with carbon / tetrahydrofuran / 35 h / 20 °C

8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C

9.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C

9.2: Cooling with ice

10.1: triphenylphosphine / dichloromethane / 0.75 h / Cooling with ice

10.2: 1 h / Cooling with ice

10.3: Cooling with ice

11.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

11.2: 0.33 h / Cooling with ice

12.1: pyridine / methanol / 20 °C

13.1: Iodine monochloride / dichloromethane / 1 h / Cooling with ice

14.1: potassium phosphate / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 1 h / 80 °C / Inert atmosphere

15.1: hydrogen / palladium on activated charcoal / tetrahydrofuran; methanol / 5 h / 20 °C / 760.05 Torr

16.1: sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 2 h / 20 °C

17.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C

18.1: trifluoroacetic acid / chloroform / 20 °C / Cooling with ice

19.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water / 20 - 70 °C

20.1: hydrogen bromide; acetic acid / water / 20 - 60 °C

With pyridine; sodium hypochlorite; sodium chlorite; potassium phosphate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,1,3,3-Tetramethyldisiloxane; hydrogen bromide; hydrogen; sodium ethanolate; Iodine monochloride; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; hydroquinone; methyl p-toluene sulfonate; triphenylphosphine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; palladium on activated charcoal; rhodium contaminated with carbon; (Ph₃P)2IrCl(CO); In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

4,4-dimethylpentanoic acid

pivalaldehyde

5-benzyloxypentanoic acid

3,4,5,6-tetrahydro-2H-pyran-2-one

Refernces