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

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

Relevant articles and documents

Asymmetric Epoxidation of Olefins Catalyzed by Substituted Aminobenzimidazole Manganese Complexes Derived from L-Proline

A family of manganese complexes [Mn(Rpeb)(OTf)2] (peb=1-(1-ethyl-1H-benzo[d]imidazol-2-yl)-N-((1-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl) pyrrolidin-2-yl)methyl)-N-methylmethanamine)) derived from L-proline has been synthesized and characterized, where R refers to the group at the diamine backbone. X-ray crystallographic analyses indicate that all the manganese complexes [Mn(Rpeb)(OTf)2] exhibit cis-α topology. These types of complexes are shown to catalyze the asymmetric epoxidation of olefins employing H2O2 as a terminal oxidant with up to 96% ee. Obviously, the R group of the diamine backbone can influence the catalytic activity and enantioselectivity in the asymmetric epoxidation of olefins. In particular, Mn(i-Prpeb)(OTf)2 bearing an isopropyl arm, cannot catalyze the epoxidation reaction with H2O2 as the oxidant. However, when PhI(OAc)2 is used as the oxidant instead, all the manganese complexes including Mn(i-Prpeb)(OTf)2 can promote the epoxidation reactions efficiently. Taken together, these results indicate that isopropyl substitution on the Rpeb ligand inhibits the formation of active Mn(V)-oxo species in the H2O2/carboxylic acid system via an acid-assisted pathway.

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.