tert-butyl (2S)-benzenesulfonylamino-3-[3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionate

Base Information

• Chemical Name: tert-butyl (2S)-benzenesulfonylamino-3-[3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionate
• CAS No.: 247034-30-6
• Molecular Formula: C₂₉H₃₅ClN₆O₅S
• Molecular Weight: 615.153

Synonyms:tert-butyl (2S)-benzenesulfonylamino-3-[3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionate

Chemical Property of tert-butyl (2S)-benzenesulfonylamino-3-[3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionate

Chemical Property:

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Technology Process of tert-butyl (2S)-benzenesulfonylamino-3-[3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionate

There total 8 articles about tert-butyl (2S)-benzenesulfonylamino-3-[3-chloro-4-{4-(pyrimidin-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: 85.0%

3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoic acid (247035-37-6) + tert-butyl (2S)-N-benzenesulfonyl-2,3-diaminopropionate hydrochloride → tert-butyl (2S)-benzenesulfonylamino-3-[3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionate (247034-30-6)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 13h;

DOI:10.1016/j.bmc.2005.10.061

Reference yield:

methyl 3-chloro-4-fluorobenzoate (234082-35-0) → tert-butyl (2S)-benzenesulfonylamino-3-[3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionate (247034-30-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 66 percent / dimethylsulfoxide / 72 h / 120 °C

2: Et₃N / CH₂Cl₂ / 1 h

3: NaN₃ / dimethylformamide / 5 h / 80 °C

4: 595 mg / H₂; AcOH / Pd/C / dioxane / 4 h / 20 °C

5: (i-Pr)2NEt / dimethylformamide / 10 h / 125 °C

6: 109 mg / NaOH / methanol; tetrahydrofuran; H₂O / 8 h / 40 °C

7: 85 percent / 1-hydroxybenzotriazole hydrate; N-methylmorpholine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 13 h

With 4-methyl-morpholine; sodium hydroxide; sodium azide; hydrogen; acetic acid; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.10.061

Reference yield:

4-HYDROXYPIPERIDINE (5382-16-1) → tert-butyl (2S)-benzenesulfonylamino-3-[3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionate (247034-30-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 66 percent / dimethylsulfoxide / 72 h / 120 °C

2: Et₃N / CH₂Cl₂ / 1 h

3: NaN₃ / dimethylformamide / 5 h / 80 °C

4: 595 mg / H₂; AcOH / Pd/C / dioxane / 4 h / 20 °C

5: (i-Pr)2NEt / dimethylformamide / 10 h / 125 °C

6: 109 mg / NaOH / methanol; tetrahydrofuran; H₂O / 8 h / 40 °C

7: 85 percent / 1-hydroxybenzotriazole hydrate; N-methylmorpholine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 13 h

With 4-methyl-morpholine; sodium hydroxide; sodium azide; hydrogen; acetic acid; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.10.061

upstream raw materials:

3-chloro-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoic acid

methyl 3-chloro-4-fluorobenzoate

4-HYDROXYPIPERIDINE

methyl 3-chloro-4-(4-hydroxypiperidin-1-yl)benzoate

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