41036-43-5

Basic information

• Product Name: benzyloxycarbonylalanine chloromethyl ketone
• Synonyms: benzyloxycarbonylalanine chloromethyl ketone
• CAS NO: 41036-43-5
• Molecular Formula: C₁₂H₁₄ClNO₃
• Molecular Weight: 255.69746
• Mol File: 41036-43-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 400.4 °C at 760 mmHg
• Flash Point: 195.9 °C
• Appearance: /
• Density: 1.22 g/cm³
• Vapor Pressure: 1.28E-06mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: benzyloxycarbonylalanine chloromethyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: benzyloxycarbonylalanine chloromethyl ketone(41036-43-5)
• EPA Substance Registry System: benzyloxycarbonylalanine chloromethyl ketone(41036-43-5)

Safety Data

• Hazardous Substances Data: 41036-43-5(Hazardous Substances Data)

Usage

Description

Benzyloxycarbonylalanine chloromethyl ketone is a chemical compound that functions as an irreversible inhibitor of serine proteases, playing a significant role in research and pharmaceutical applications.
Used in Research Applications:
Benzyloxycarbonylalanine chloromethyl ketone is used as a research tool for studying the mechanisms of serine proteases, as it irreversibly binds to their active sites and inhibits their activity. This helps researchers understand the role of these enzymes in various biological processes.
Used in Pharmaceutical Applications:
Benzyloxycarbonylalanine chloromethyl ketone is used as a starting point for developing potential therapeutic agents targeting serine proteases. By inhibiting the activity of these enzymes, it may contribute to the treatment of diseases where serine proteases play a crucial role.
Used in Drug Development:
In the pharmaceutical industry, benzyloxycarbonylalanine chloromethyl ketone is used as a lead compound for designing drugs that modulate the activity of serine proteases. This can lead to the development of new treatments for a variety of conditions.
However, it is important to handle benzyloxycarbonylalanine chloromethyl ketone with caution due to its potential toxicity and reactivity.

InChI:InChI=1/C12H14ClNO3/c1-9(11(15)7-13)14-12(16)17-8-10-5-3-2-4-6-10/h2-6,9H,7-8H2,1H3,(H,14,16)/t9-/m0/s1

Upstream product

• 67865-68-3 benzyl (S)-(4-diazo-3-oxobutan-2-yl)carbamate 
• 186581-53-3 diazomethane 
• 1142-20-7 N-Cbz-Ala 
• 1168-87-2 benzyloxycarbonylalanine p-nitrophenyl ester 
• 28819-05-8 (S)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 676486-18-3 benzyl (S)-(4-(dimethyl(oxo)-λ⁶-sulfaneylidene)-3-oxobutan-2-yl)carbamate 

Downstream Products

• 116835-55-3 2-((S)-3-Benzyloxycarbonylamino-2-oxo-butyl)-malonic acid dimethyl ester 
• 70772-04-2 (1-Methylene-2-oxo-propyl)-carbamic acid benzyl ester 
• 54680-72-7 AlaCH₃, HCl 
• 51152-30-8 H-AlaCH₂Cl, HBr 
• 159141-65-8 (2S,3S)-1-chloro-3-(benzyloxycarbonylamino)-2-butanol 
• 945606-91-7 C₁₂H₁₆NO₃Cl 
• 159141-73-8 threo N-Cbz-alanyl epoxide 
• 116835-56-4 Z-AlaΨ(COCH2)Gly 
• 116835-63-3 Z-AlaΨ(COCH2)(RS)Ala 
• 116835-65-5 Z-AlaΨ(COCH2)(RS)Asp 
• 116835-57-5 2-((S)-3-Benzyloxycarbonylamino-2-oxo-butyl)-2-methyl-malonic acid dimethyl ester 
• 116835-67-7 Z-AlaΨ(COCH2)(RS)Phe 
• 116835-58-6 2-((S)-3-Benzyloxycarbonylamino-2-oxo-butyl)-2-methoxycarbonyl-succinic acid dimethyl ester 
• 116835-69-9 Z-AlaΨ(COCH2)(RS)Trp 

Relevant articles and documents

Rhodium(III)-catalyzed C–H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles

The synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles via rhodium(III)-catalyzed C–H functionalization of C-alkenyl azoles with sulfoxonium ylides is disclosed. Reactions proceeded in good to high yields for a range of aryl, heteroaryl and alkyl sulfoxonium ylides. In addition, 2-alkenyl imidazoles with different substitution patterns as well as C-alkenyl triazoles were effective inputs. The reaction could also be performed under straightforward bench top conditions.

Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases

Seven PNA-encoded combinatorial libraries targeting proteases and phosphatases with covalent reversible and irreversible mechanism-based inhibitors were prepared. The libraries were synthesized using modified PNA monomers, which dramatically increase the water solubility of the libraries in biologically relevant buffers. The libraries were shown to selectively inhibit targeted enzymes.

One-Carbon Chain Extension of Esters to α-Chloroketones: A Safer Route without Diazomethane

The reaction of a variety of methyl esters with dimethylsulfoxonium methylide at 0-25 °C affords the chain-extended β-keto dimethylsulfoxonium ylides. Subsequent treatment with hydrogen chloride in THF proceeds with loss of DMSO to afford the corresponding α-chloroketones. This sequence has been utilized to convert the methyl esters of CBZ-protected alanine and valine to the anti N-protected α-amino epoxides, which are important pharmaceutical intermediates. When the same protocol is applied to BOC-protected phenylalanine methyl ester, epimerization occurs so that the use of a more reactive aryl ester is required. This chemistry provides a practical route to α-chloroketones that avoids the use of toxic and explosive diazomethane.