247068-83-3

Basic information

• Product Name: CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester
• Synonyms: CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester;N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl este;N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester;[(1S)-3-Methyl-1-[[(2S)-2-methyloxiranyl]carbonyl]butyl]-carbamic Acid 1,1-Dimethylethyl Ester;tert-Butyl ((S)-4-methyl-1-((S)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate
• CAS NO: 247068-83-3
• Molecular Formula: C14H25NO4
• Molecular Weight: 271.3526
• Mol File: 247068-83-3.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 369.8±37.0 °C(Predicted)
• Appearance: /
• Density: 1.061±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 11.08±0.46(Predicted)
• CAS DataBase Reference: CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester(247068-83-3)
• EPA Substance Registry System: CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester(247068-83-3)

Safety Data

• Hazardous Substances Data: 247068-83-3(Hazardous Substances Data)

Usage

Description

CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-dimethylethyl ester, also known as a key intermediate in the synthesis of epoxomicin, is a complex organic compound with potential applications in the pharmaceutical industry. It is characterized by its unique molecular structure, which includes a carbamic acid group and an ester functional group, contributing to its reactivity and versatility in chemical reactions.

Uses

Used in Pharmaceutical Industry:
CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-dimethylethyl ester is used as a reagent for the synthesis of epoxomicin, a potent proteasome inhibitor with antitumor, anti-inflammatory, and antibiotic properties. Its role in the synthesis process is crucial, as it contributes to the formation of the final product, which has significant therapeutic applications.
In the synthesis of epoxomicin, this compound serves as a building block, providing the necessary structural elements for the formation of the final molecule. The proteasome inhibition activity of epoxomicin makes it a valuable compound in the development of treatments for various types of cancer, as it can help to regulate cellular processes and inhibit tumor growth.
Additionally, the anti-inflammatory and antibiotic properties of epoxomicin suggest that CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2S)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-dimethylethyl ester may also have applications in the development of drugs for inflammatory conditions and bacterial infections. Further research and development in these areas could potentially lead to new therapeutic options for patients suffering from these conditions.

Upstream product

• 87694-50-6 N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 247068-81-1 tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate 
• 54430-65-8 [(R)-1-(Imidazole-1-carbonyl)-3-methyl-butyl]-carbamic acid tert-butyl ester 
• 16937-99-8 N-Boc-D-Leu 
• 338972-00-2 Boc-Leu-Cl 
• 173899-64-4 (S)-tert-butyl (4-methyl-1-morpholino-1-oxopentan-2-yl)carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 61-90-5 L-leucine 
• 1609959-47-8 tert-butyl N-[(2S)-1-(-2-methyloxirane-2-yl)-1-hydroxy-4-methylpentan-2-yl]carbamate 
• 1609959-45-6 tert-butyl N-[(4S)-3-hydroxy-2,6-dimethylhept-1-en-4-yl]carbamate 
• 247068-85-5 (S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one trifluoroacetic acid salt 
• 1186298-17-8 (1-isobutyl-3-methyl-2-oxo-but-3-enyl)carbamic acid tert-butyl ester 
• 75-65-0 tert-butyl alcohol 

Relevant articles and documents

Macrocyclic Immunoproteasome Inhibitors as a Potential Therapy for Alzheimer's Disease

Previously, we reported that immunoproteasome (iP)-targeting linear peptide epoxyketones improve cognitive function in mouse models of Alzheimer's disease (AD) in a manner independent of amyloid β. However, these compounds' clinical prospect for AD is limited due to potential issues, such as poor brain penetration and metabolic instability. Here, we report the development of iP-selective macrocyclic peptide epoxyketones prepared by a ring-closing metathesis reaction between two terminal alkenes attached at the P2 and P3/P4 positions of linear counterparts. We show that a lead macrocyclic compound DB-60 (20) effectively inhibits the catalytic activity of iP in ABCB1-overexpressing cells (IC50: 105 nM) and has metabolic stability superior to its linear counterpart. DB-60 (20) also lowered the serum levels of IL-1α and ameliorated cognitive deficits in Tg2576 mice. The results collectively suggest that macrocyclic peptide epoxyketones have improved CNS drug properties than their linear counterparts and offer promising potential as an AD drug candidate.

Preparation method of carfilzomib intermediate

The invention relates to a preparation method of a carfilzomib intermediate F, and belongs to the field of medicinal chemistry. The preparation method comprises the following steps: by taking t-butyloxycarbonyl-L-leucine as a starting material, carrying out condensation, Grignard reaction, reduction, epoxidation, oxidation and salt forming reaction to obtain a carfilzomib key intermediate F. The method has the advantages of mild reaction conditions, high yield, good selectivity and less generated three wastes, and is suitable for industrial amplification production.

Continuous Process Improvement in the Manufacture of Carfilzomib, Part 2: An Improved Process for Synthesis of the Epoxyketone Warhead

The development and kilogram-scale demonstration of an improved process for the synthesis of the epoxyketone warhead of carfilzomib is described. Critical to the success of this process was: (1) development of a scalable asymmetric epoxidation protocol; (2) identification of a crystalline intermediate with improved physical properties for isolation; (3) discovery and optimization of epimerization conditions to set the target stereochemistry; and (4) introduction of a seeded-bed coaddition crystallization to facilitate isolation of the final low-melting target. The results of kilogram-scale demonstration runs are shared, including details of a continuous process for the safe execution of an exothermic Barbier-type Grignard process.