(2S)-benzenesulfonylamino-3-[3-hydroxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionic acid

Base Information

• Chemical Name: (2S)-benzenesulfonylamino-3-[3-hydroxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionic acid
• CAS No.: 247034-74-8
• Molecular Formula: C₂₅H₂₈N₆O₆S
• Molecular Weight: 540.6
• Mol file: 247034-74-8.mol

Synonyms:(2S)-benzenesulfonylamino-3-[3-hydroxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionic acid

Chemical Property of (2S)-benzenesulfonylamino-3-[3-hydroxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-benzenesulfonylamino-3-[3-hydroxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionic acid

There total 10 articles about (2S)-benzenesulfonylamino-3-[3-hydroxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionic 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: 40.0%

tert-butyl (2S)-benzenesulfonylamino-3-[3-methoxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionate (247034-71-5) → (2S)-benzenesulfonylamino-3-[3-hydroxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionic acid (247034-74-8)

Guidance literature:

With boron tribromide; In dichloromethane; 1,2-dichloro-ethane; at 40 ℃; for 7h;

DOI:10.1016/j.bmc.2005.10.061

Reference yield:

4-HYDROXYPIPERIDINE (5382-16-1) → (2S)-benzenesulfonylamino-3-[3-hydroxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionic acid (247034-74-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 47 percent / dimethylsulfoxide / 72 h / 120 °C

2: Et₃N / CH₂Cl₂ / 1 h

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

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

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

6: 261 mg / NaOH / methanol; tetrahydrofuran; H₂O / 8 h / 40 °C

7: 100 percent / 1-hydroxybenzotriazole hydrate; N-methylmorpholine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 13 h

8: 40 percent / BBr₃ / 1,2-dichloro-ethane; CH₂Cl₂ / 7 h / 40 °C

With 4-methyl-morpholine; sodium hydroxide; sodium azide; hydrogen; boron tribromide; 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; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.10.061

Reference yield:

methyl 4-(4-hydroxypiperidin-1-yl)-3-methoxybenzoate (247035-42-3) → (2S)-benzenesulfonylamino-3-[3-hydroxy-4-{4-(pyrimidin-2-ylamino)piperidin-1-yl}benzoylamino]propionic acid (247034-74-8)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N / CH₂Cl₂ / 1 h

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

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

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

5: 261 mg / NaOH / methanol; tetrahydrofuran; H₂O / 8 h / 40 °C

6: 100 percent / 1-hydroxybenzotriazole hydrate; N-methylmorpholine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 13 h

7: 40 percent / BBr₃ / 1,2-dichloro-ethane; CH₂Cl₂ / 7 h / 40 °C

With 4-methyl-morpholine; sodium hydroxide; sodium azide; hydrogen; boron tribromide; 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; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.10.061

upstream raw materials:

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

4-HYDROXYPIPERIDINE

methyl 4-(4-aminopiperidin-1-yl)-3-methoxybenzoate

methyl 4-(4-hydroxypiperidin-1-yl)-3-methoxybenzoate