tert-butyl 4-[3-(N,N-dimethylcarbamoyloxy)phenylcarbamoyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-[3-(N,N-dimethylcarbamoyloxy)phenylcarbamoyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-1-carboxylate
• CAS No.: 1192189-83-5
• Molecular Formula: C₄₃H₄₇N₅O₅
• Molecular Weight: 713.877

Synonyms:tert-butyl 4-[3-(N,N-dimethylcarbamoyloxy)phenylcarbamoyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-1-carboxylate

Chemical Property of tert-butyl 4-[3-(N,N-dimethylcarbamoyloxy)phenylcarbamoyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-1-carboxylate

Chemical Property:

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Technology Process of tert-butyl 4-[3-(N,N-dimethylcarbamoyloxy)phenylcarbamoyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-1-carboxylate

There total 4 articles about tert-butyl 4-[3-(N,N-dimethylcarbamoyloxy)phenylcarbamoyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]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: 43.0%

1-(tert-butoxycarbonyl)-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-4-carboxylic acid (1192189-82-4) + Dimethylcarbaminsaeure-3-aminophenylester (19962-04-0) → tert-butyl 4-[3-(N,N-dimethylcarbamoyloxy)phenylcarbamoyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-1-carboxylate (1192189-83-5)

Guidance literature:

1-(tert-butoxycarbonyl)-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-4-carboxylic acid; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In Isopropyl acetate; for 0.0833333h;

Dimethylcarbaminsaeure-3-aminophenylester; In Isopropyl acetate; at 90 ℃; for 2h;

Reference yield:

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (142851-03-4) → tert-butyl 4-[3-(N,N-dimethylcarbamoyloxy)phenylcarbamoyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-1-carboxylate (1192189-83-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: lithium hydroxide; water / tetrahydrofuran; methanol / Inert atmosphere; Reflux

2.2: pH 5 - 6

3.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / Isopropyl acetate / 0.08 h / Inert atmosphere

3.2: 2 h / 90 °C / Inert atmosphere

With water; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; Isopropyl acetate;

DOI:10.1021/ml500367g

Reference yield:

4-chloromethyl-1-tritylimidazole (103057-10-9) → tert-butyl 4-[3-(N,N-dimethylcarbamoyloxy)phenylcarbamoyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-1-carboxylate (1192189-83-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: lithium hydroxide; water / tetrahydrofuran; methanol / Inert atmosphere; Reflux

2.2: pH 5 - 6

3.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / Isopropyl acetate / 0.08 h / Inert atmosphere

3.2: 2 h / 90 °C / Inert atmosphere

With water; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; Isopropyl acetate;

DOI:10.1021/ml500367g

upstream raw materials:

1-(tert-butoxycarbonyl)-4-[(1-trityl-1H-imidazol-4-yl)methyl]piperidine-4-carboxylic acid

Dimethylcarbaminsaeure-3-aminophenylester

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

4-chloromethyl-1-tritylimidazole

Downstream raw materials:

3-{4-[(1H-imidazol-4-yl)methyl]piperidine-4-carboxamido}phenyl N,N-dimethylcarbamate

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