1-Pentanone, 2-aMino-4-Methyl-1-[(2R)-2-Methyloxiranyl]-, (2S)-, trifluoroacetate (9CI)

Base Information

• Chemical Name: 1-Pentanone, 2-aMino-4-Methyl-1-[(2R)-2-Methyloxiranyl]-, (2S)-, trifluoroacetate (9CI)
• CAS No.: 247068-85-5
• Molecular Formula: C9H17NO2.C2HF3O2
• Molecular Weight: 285.26000
• Mol file: 247068-85-5.mol

Synonyms:Carfilzomib intermediate;1-Pentanone, 2-amino-4-methyl-1-[(2R)-2-methyl-2-oxiranyl]-, (2S)-, 2,2,2-trifluoroacetate (1:1);

Chemical Property of 1-Pentanone, 2-aMino-4-Methyl-1-[(2R)-2-Methyloxiranyl]-, (2S)-, trifluoroacetate (9CI)

Chemical Property:

• Melting Point: 120 - 123° C
• PSA: 92.92000
• LogP: 2.05140
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

(2S)-2-Amino-4-methyl-1-[(2R)-2-methyloxiranyl]-1-pentanoneTrifluoroacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S)-2-Amino-4-methyl-1-[(2R)-2-methyloxiranyl]-1-pentanone Trifluoroacetate is an intermediate of Carfilzomib (C183460) which is a second-generation proteasome inhibitor that is used as a treatment in relapsed and refractory multiple myeloma.

Technology Process of 1-Pentanone, 2-aMino-4-Methyl-1-[(2R)-2-Methyloxiranyl]-, (2S)-, trifluoroacetate (9CI)

There total 39 articles about 1-Pentanone, 2-aMino-4-Methyl-1-[(2R)-2-Methyloxiranyl]-, (2S)-, trifluoroacetate (9CI) 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: 100.0%

benzyl ((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate + trifluoroacetic acid (76-05-1) → (S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one trifluoroacetic acid salt (247068-85-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; at 20 ℃; for 1.33333h; under 760.051 Torr; Inert atmosphere;

DOI:10.1021/ja109377p

Reference yield: 88.0%

trifluoroacetic acid (76-05-1) + tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate (247068-82-2,247068-83-3) → (S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one trifluoroacetic acid salt (247068-85-5)

Guidance literature:

In dichloromethane; at 20 ℃; for 4h;

Reference yield: 82.0%

2-(dibenzylamino)-4-methyl-1-((R)-2-methyloxiran-2-yl)pentanal + trifluoroacetic acid (76-05-1) → (S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one trifluoroacetic acid salt (247068-85-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 24h;

upstream raw materials:

trifluoroacetic acid

tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Z-Leu-OH

(S)-benzyl (2,6-dimethyl-3-oxohept-1-en-4-yl)carbamate

Downstream raw materials:

C₃₄H₅₃N₅O₆

tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

carfilzomib

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

Refernces

• 1、 Zhang, Wen,Wang, Xueyuan,Zhang, Haoyang,Wen, Tiantian,Yang, Lin,Miao, Hang,Wang, Jia,Liu, Hailong,Yang, Xu,Lei, Meng,Zhu, Yongqiang. "Discovery of novel tripeptide propylene oxide proteasome inhibitors for the treatment of multiple myeloma". . . Retrieved 2021/05/13.
• 2、 -. "Preparation method of carfilzomib intermediate". Paragraph 0119-0121. . Retrieved 2021/08/06.