Bortezomib intermediates II

Base Information

• Chemical Name: Bortezomib intermediates II
• CAS No.: 205393-21-1
• Molecular Formula: C24H37BN2O3.ClH
• Molecular Weight: 448.841
• Mol file: 205393-21-1.mol

Synonyms:Benzenepropanamide,a-amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-,monohydrochloride, (aS)- (9CI);Benzenepropanamide, a-amino-N-[1-(hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl)-3-methylbutyl]-,monohydrochloride, [3aS-[2[S*(R*)],3aa,4b,6b,7aa]]-;

Chemical Property of Bortezomib intermediates II

Chemical Property:

• Melting Point: 197-198 °C
• PSA: 77.07000
• LogP: 6.11730
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

99% ^*data from raw suppliers

(αS)-α-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-benzenepropanamideMonohydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (αS)-α-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-benzenepropanamide Monohydrochloride is a Bortezomib (B675700) intermediate which is used in the evaluation of bone-targeted proteasome inhibitors for myeloma.

Technology Process of Bortezomib intermediates II

There total 5 articles about Bortezomib intermediates II 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: 80.6%

hydrogenchloride (7647-01-0,15364-23-5) + (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate (1187479-72-6) → 2-amino-N-((R)-3-methyl-1-((3aS,4S,6R,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-3-phenylpropanamide hydrochloride (205393-21-1)

Guidance literature:

In dichloromethane; ethyl acetate; at 20 ℃; for 2h; Cooling;

DOI:10.1016/j.bmc.2018.06.020

Reference yield: 79.1%

(1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate (1187479-72-6) + (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate → 2-amino-N-((R)-3-methyl-1-((3aS,4S,6R,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-3-phenylpropanamide hydrochloride (205393-21-1) + (1S,2S,3R,5S)-pinanediol L-phenylalanine-L-leucine boronate hydrochloride

Guidance literature:

With hydrogenchloride; In ethyl acetate; at -0.9 - 14.8 ℃; for 4.55h; Industry scale;

Reference yield:

(1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate (1187479-72-6) → 2-amino-N-((R)-3-methyl-1-((3aS,4S,6R,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-3-phenylpropanamide hydrochloride (205393-21-1)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 2h; Cooling;

DOI:10.1039/c8ob02668h

upstream raw materials:

(1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate

hydrogenchloride

(aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

Refernces

• 1、 Lei, Meng,Feng, Huayun,Bai, Enhe,Zhou, Hui,Wang, Jia,Shi, Jingmiao,Wang, Xueyuan,Hu, Shihe,Liu, Zhaogang,Zhu, Yongqiang. "Design, synthesis, in vitro and in vivo evaluation, and structure-activity relationship (SAR) discussion of novel dipeptidyl boronic acid proteasome inhibitors as orally available anti-cancer agents for the treatment of multiple myeloma and mechanism studies". supporting information. p. 3975 - 3981. Retrieved 2018/06/25.
• 2、 -. "SYNTHESIS OF BORONIC ESTER AND ACID COMPOUNDS". Page/Page column 44-45. . Retrieved 2010/02/14.