ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

Base Information

• Chemical Name: ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate
• CAS No.: 1334531-21-3
• Molecular Formula: C₃₂H₄₃ClN₂O₆
• Molecular Weight: 587.156

Synonyms:ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

Chemical Property of ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

Chemical Property:

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Technology Process of ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

There total 8 articles about ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-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: 72.0%

4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoicacid (1334531-20-2) + (S)-(+)-nipecotic acid ethyl ester (37675-18-6) → ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate (1334531-21-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1016/j.bmc.2011.07.007

Reference yield:

N-[4-chloro-2-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide (1007652-06-3) → ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate (1334531-21-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sec.-butyllithium / tetrahydrofuran; hexane; cyclohexane / 0.5 h / -78 - 20 °C

1.2: 1.5 h / -78 - -50 °C

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 4 h / 0 - 50 °C

2.2: 0.08 h

3.1: Chiralcel OD column / hexane; isopropyl alcohol / 20 °C / Resolution of racemate; HPLC conditions

4.1: sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Cooling with ice

5.1: water; potassium carbonate / methanol / 2.5 h / 60 °C

6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2.5 h / 20 °C

With water; sec.-butyllithium; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; isopropyl alcohol; toluene;

DOI:10.1016/j.bmc.2011.07.007

Reference yield:

N-(4-chloro-2-[hydroxy(2-methoxyphenyl)methyl]-6-(trifluoromethyl)phenyl)-2,2-dimethylpropanamide (1334531-17-7) → ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate (1334531-21-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 4 h / 0 - 50 °C

1.2: 0.08 h

2.1: Chiralcel OD column / hexane; isopropyl alcohol / 20 °C / Resolution of racemate; HPLC conditions

3.1: sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Cooling with ice

4.1: water; potassium carbonate / methanol / 2.5 h / 60 °C

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2.5 h / 20 °C

With water; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; hexane; dichloromethane; isopropyl alcohol; toluene;

DOI:10.1016/j.bmc.2011.07.007

upstream raw materials:

N-[4-chloro-2-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide

N-(4-chloro-2-[hydroxy(2-methoxyphenyl)methyl]-6-(trifluoromethyl)phenyl)-2,2-dimethylpropanamide

(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-methylphenyl)(2-methoxyphenyl)methanol

methyl 4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methylphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate

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