tert-butyl (2S)-benzenesulfonylamino-3-[4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoylamino]propionate

Base Information

• Chemical Name: tert-butyl (2S)-benzenesulfonylamino-3-[4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoylamino]propionate
• CAS No.: 883726-99-6
• Molecular Formula: C₂₈H₃₈N₆O₅S
• Molecular Weight: 570.713

Synonyms:tert-butyl (2S)-benzenesulfonylamino-3-[4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoylamino]propionate

Chemical Property of tert-butyl (2S)-benzenesulfonylamino-3-[4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoylamino]propionate

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Technology Process of tert-butyl (2S)-benzenesulfonylamino-3-[4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoylamino]propionate

There total 8 articles about tert-butyl (2S)-benzenesulfonylamino-3-[4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoylamino]propionate 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: 29.0%

4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoic acid (883726-98-5) + tert-butyl (2S)-N-benzenesulfonyl-2,3-diaminopropionate hydrochloride → tert-butyl (2S)-benzenesulfonylamino-3-[4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoylamino]propionate (883726-99-6)

Guidance literature:

4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h;

tert-butyl (2S)-N-benzenesulfonyl-2,3-diaminopropionate hydrochloride; In N,N-dimethyl-formamide; at 60 ℃; for 15h;

DOI:10.1016/j.bmc.2005.10.061

Reference yield:

ethyl 4-(4-aminopiperidin-1-yl)benzoate (247034-88-4) → tert-butyl (2S)-benzenesulfonylamino-3-[4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoylamino]propionate (883726-99-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / tetrahydrofuran / 19 h / 20 °C

2.1: EtBr / ethanol / 13 h / Heating

2.2: CF₃CO₂H / H₂O / 3 h / 20 °C

2.3: 61 percent / NaOEt / ethanol / 16 h

3.1: 100 percent / NaOH / methanol; tetrahydrofuran; H₂O / 8 h / 40 °C

4.1: 1,1'-carbonyldiimidazole / dimethylformamide / 1.5 h / 20 °C

4.2: 29 percent / dimethylformamide / 15 h / 60 °C

With sodium hydroxide; ethidium Bromide; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.10.061

Reference yield:

4-HYDROXYPIPERIDINE (5382-16-1) → tert-butyl (2S)-benzenesulfonylamino-3-[4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoylamino]propionate (883726-99-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 77 percent / dimethylsulfoxide / 72 h / 120 °C

2.1: 51 percent / P(n-Bu)3; 1,1'-(azodicarbonyl)dipiperidine / benzene / 23 h / 0 - 20 °C

3.1: 99 percent / hydrazine monohydrate / methanol / 16 h / 20 °C

4.1: 92 percent / tetrahydrofuran / 19 h / 20 °C

5.1: EtBr / ethanol / 13 h / Heating

5.2: CF₃CO₂H / H₂O / 3 h / 20 °C

5.3: 61 percent / NaOEt / ethanol / 16 h

6.1: 100 percent / NaOH / methanol; tetrahydrofuran; H₂O / 8 h / 40 °C

7.1: 1,1'-carbonyldiimidazole / dimethylformamide / 1.5 h / 20 °C

7.2: 29 percent / dimethylformamide / 15 h / 60 °C

With sodium hydroxide; tributylphosphine; ethidium Bromide; hydrazine hydrate; 1,1'-carbonyldiimidazole; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; methanol; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.bmc.2005.10.061

upstream raw materials:

4-{4-(4,5-dihydro-1H-imidazol-2-ylamino)piperidin-1-yl}benzoic acid

ethyl 4-(4-aminopiperidin-1-yl)benzoate

4-HYDROXYPIPERIDINE

ethyl 4-(4-phthalimidopiperidin-1-yl)benzoate

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