Bortezomib Impurity 9

Base Information

• Chemical Name: Bortezomib Impurity 9
• CAS No.: 1194235-41-0
• Molecular Formula: C28H34BN5O5
• Molecular Weight: 531.41
• Mol file: 1194235-41-0.mol

Synonyms:Bortezomib Impurity 9

Chemical Property of Bortezomib Impurity 9

Chemical Property:

• PKA: 9.69±0.43(Predicted)
• PSA: 153.54000
• Density: 1.227±0.06 g/cm3(Predicted)
• LogP: 2.68070

Purity/Quality:

99% ^*data from raw suppliers

N-(2-Pyrazinylcarbonyl)-L-phenylalanyl-N-[(1R)-1-borono-3-methylbutyl]-L-phenylalaninamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-(2-Pyrazinylcarbonyl)-L-phenylalanyl-N-[(1R)-1-borono-3-methylbutyl]-L-phenylalaninamide is an impurity of Bortezomib (B675700) and a tripeptide boronic acid proteasome inhibitor used as an antitumor agent.

Technology Process of Bortezomib Impurity 9

There total 6 articles about Bortezomib Impurity 9 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: 72.1%

(+)-pinanediol N-(2-pyrazinecarbonyl)-L-phenylalanine-L-phenylalanine-L-leucineboronate (1194235-28-3) → N-(2-pyrazinecarbonyl)-L-phenylalanine-L-phenylalanine-L-leucineboronic acid (1194235-41-0)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.bmc.2009.08.023

Reference yield:

(S)-methyl 3-phenyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)-propanoate (1194235-01-2) → N-(2-pyrazinecarbonyl)-L-phenylalanine-L-phenylalanine-L-leucineboronic acid (1194235-41-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / acetone / pH 12 - Ca_. 13 / Cooling with ice

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / tetrahydrofuran / 0.5 h / -20 °C

2.2: -20 °C

3.1: ammonium acetate; sodium periodate / acetone / 10 h / 20 °C

With sodium periodate; ammonium acetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; acetone;

Reference yield:

(S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid (114457-94-2,1608986-16-8) → N-(2-pyrazinecarbonyl)-L-phenylalanine-L-phenylalanine-L-leucineboronic acid (1194235-41-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; hydrogenchloride / tetrahydrofuran / 2 h / 0 °C / pH 12 - Ca_. 13

2.1: sodium hydroxide / acetone / pH 12 - Ca_. 13 / Cooling with ice

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / tetrahydrofuran / 0.5 h / -20 °C

3.2: -20 °C

4.1: ammonium acetate; sodium periodate / acetone / 10 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; sodium periodate; ammonium acetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; acetone;

upstream raw materials:

(+)-pinanediol N-(2-pyrazinecarbonyl)-L-phenylalanine-L-phenylalanine-L-leucineboronate

(S)-methyl 3-phenyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)-propanoate

(S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid

N-(2-pyrazinecarbonyl)-L-phenylalanine-L-phenylalanine