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

Base Information

• Chemical Name: 4-(4-azidophenylsulfonyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid
• CAS No.: 1438386-15-2
• Molecular Formula: C₁₇H₂₂N₄O₆S
• Molecular Weight: 410.451

Synonyms:4-(4-azidophenylsulfonyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

Chemical Property of 4-(4-azidophenylsulfonyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

Chemical Property:

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Technology Process of 4-(4-azidophenylsulfonyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

There total 6 articles about 4-(4-azidophenylsulfonyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic 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: 70.0%

4-(4-aminophenylsulfonyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1458054-94-8) → 4-(4-azidophenylsulfonyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1438386-15-2)

Guidance literature:

With tert.-butylnitrite; trimethylsilylazide; In acetonitrile; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1039/c3ob41046c

Reference yield:

1-tert-butyl 4-ethyl 4-((4-nitrophenyl)sulfanyl)piperidine-1,4-dicarboxylate (1438386-11-8) → 4-(4-azidophenylsulfonyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1438386-15-2)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C

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

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

With tert.-butylnitrite; trimethylsilylazide; water; hydrogen; palladium; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In ethanol; dichloromethane; acetonitrile;

DOI:10.1039/c3ob41046c

Reference yield:

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (142851-03-4) → 4-(4-azidophenylsulfonyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1438386-15-2)

Guidance literature:

Multi-step reaction with 5 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

With tert.-butylnitrite; trimethylsilylazide; water; hydrogen; palladium; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; 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:

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

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

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

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

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