CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester

Base Information

• Chemical Name: CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester
• CAS No.: 247068-82-2
• Molecular Formula: C14H25NO4
• Molecular Weight: 271.357
• Mol file: 247068-82-2.mol

Synonyms:CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester;tert-butyl (S)-4-Methyl-1-((R)-2-Methyloxiran-2-yl)-1-oxopentan-2-ylcarbaMate;N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-CarbaMic acid, 1,1-diMethylethyl ester;Boc-L-leucine epoxyketone;[(1S)-3-Methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]carbamic acid 1,1-dimethylethyl ester;Boc-leucine-epoxyketone;Boc-LeuEK(tert-butyl (S)-4-Methyl-1-((R)-2-Methyloxiran-2-yl)-1-oxopentan-2-ylcarbaMate );[(1S)-3-Methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]carbamic

Chemical Property of CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester

Chemical Property:

• Boiling Point: 369.8±37.0 °C(Predicted)
• PKA: 11.08±0.46(Predicted)
• PSA: 67.93000
• Density: 1.061±0.06 g/cm3(Predicted)
• LogP: 2.67470
• Storage Temp.: 2-8°C

Purity/Quality:

tert-Butyl((S)-4-Methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl ((S)-4-Methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate 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 CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester

There total 26 articles about CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester 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: 91.0%

tert-butyl {(1S,2S)-1-hydroxy-4-methyl-1-[(R)-2-methyloxiran-2-yl]pentan-2-yl}carbamate → tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate (247068-82-2,247068-83-3)

Guidance literature:

With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 ℃; Green chemistry;

DOI:10.3184/174751916X14539789662063

Reference yield: 85.0%

tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate (247068-81-1) → tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate (247068-82-2,247068-83-3)

Guidance literature:

With (R)-La-BINOL; triphenylphosphine; tert-butyl alcohol; In toluene; at 20 ℃; for 0.5h; Solvent;

Reference yield: 84.0%

tert-butyl ((R)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate (247068-83-3) → tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate (247068-82-2,247068-83-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tert-butyl methyl ether; at 20 ℃; for 12h;

upstream raw materials:

tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate

N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide

(1-isobutyl-3-methyl-2-oxo-but-3-enyl)carbamic acid tert-butyl ester

N-tert-butoxycarbonyl-L-leucine

Downstream raw materials:

C₁₆H₂₀BrNO₃

carfilzomib

(S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2yl)pentan-1-one trifluoroacetic acid

C₂₆H₃₉N₃O₆

Refernces

• 1、 Beaver, Matthew G.,Shi, Xianqing,Riedel, Jan,Patel, Parth,Zeng, Alicia,Corbett, Michael T.,Robinson, Jo Anna,Parsons, Andrew T.,Cui, Sheng,Baucom, Kyle,Lovette, Michael A.,I?ten, El?in,Brown, Derek B.,Allian, Ayman,Flick, Tawnya G.,Chen, Wendy,Yang, Ning,Walker, Shawn D.. "Continuous Process Improvement in the Manufacture of Carfilzomib, Part 2: An Improved Process for Synthesis of the Epoxyketone Warhead". . p. 490 - 499. Retrieved 2020.
• 2、 Lee, Min Jae,Bhattarai, Deepak,Jang, Hyeryung,Baek, Ahreum,Yeo, In Jun,Lee, Seongsoo,Miller, Zachary,Lee, Sukyeong,Hong, Jin Tae,Kim, Dong-Eun,Lee, Wooin,Kim, Kyung Bo. "Macrocyclic Immunoproteasome Inhibitors as a Potential Therapy for Alzheimer's Disease". . p. 10934 - 10950. Retrieved 2021/08/20.