tert-butyl 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-phenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-phenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-carboxylate
• CAS No.: 1438386-23-2
• Molecular Formula: C₃₀H₃₆FN₅O₇S
• Molecular Weight: 629.71

Synonyms:tert-butyl 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-phenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-carboxylate

Chemical Property of tert-butyl 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-phenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-phenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-carboxylate

There total 8 articles about tert-butyl 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-phenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-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: 64.0%

1-ethynyl-3-fluoro-benzene (2561-17-3) + tert-butyl 4-(4-azidophenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-carboxylate (1438386-16-3) → tert-butyl 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-phenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-carboxylate (1438386-23-2)

Guidance literature:

With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1039/c3ob41046c

Reference yield:

1-tert-butyl 4-ethyl 4-((4-nitrophenyl)sulfanyl)piperidine-1,4-dicarboxylate (1438386-11-8) → tert-butyl 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-phenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-carboxylate (1438386-23-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydroxide; water / ethanol / 48 h / 20 °C

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C

3.1: palladium; hydrogen / ethanol / 72 h / 20 °C / 3102.97 Torr

4.1: trimethylsilylazide; tert.-butylnitrite / acetonitrile / 2.5 h / 0 - 20 °C / Inert atmosphere

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / N,N-dimethyl-formamide / 0.17 h / 20 °C

5.2: 20 °C

6.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With 4-methyl-morpholine; tert.-butylnitrite; copper(ll) sulfate pentahydrate; trimethylsilylazide; water; hydrogen; benzotriazol-1-ol; palladium; sodium L-ascorbate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c3ob41046c

Reference yield:

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (142851-03-4) → tert-butyl 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-phenylsulfonyl)-4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)piperidine-1-carboxylate (1438386-23-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: sodium hydroxide; water / ethanol / 48 h / 20 °C

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C

4.1: palladium; hydrogen / ethanol / 72 h / 20 °C / 3102.97 Torr

5.1: trimethylsilylazide; tert.-butylnitrite / acetonitrile / 2.5 h / 0 - 20 °C / Inert atmosphere

6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / N,N-dimethyl-formamide / 0.17 h / 20 °C

6.2: 20 °C

7.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With 4-methyl-morpholine; tert.-butylnitrite; copper(ll) sulfate pentahydrate; trimethylsilylazide; water; hydrogen; benzotriazol-1-ol; palladium; sodium L-ascorbate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c3ob41046c

upstream raw materials:

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

1-tert-butyl 4-ethyl 4-((4-nitrophenyl)sulfanyl)piperidine-1,4-dicarboxylate

1-(tert-butoxycarbonyl)-4-(4-nitrophenylthio)piperidine-4-carboxylic acid

1-(tert-butoxycarbonyl)-4-(4-nitrophenylsulfonyl)piperidine-4-carboxylic acid

Downstream raw materials:

4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)phenylsulfonyl)-N-hydroxypiperidine-4-carboxamide hydrochloride

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