Tosylphenylalanyl chloromethyl ketone

Base Information

• Chemical Name: Tosylphenylalanyl chloromethyl ketone
• CAS No.: 402-71-1
• Deprecated CAS: 130021-38-4
• Molecular Formula: C17H18ClNO3S
• Molecular Weight: 351.87
• Hs Code.: 29350090
• European Community (EC) Number: 206-954-6
• NSC Number: 727365
• UNII: P598716LJT
• DSSTox Substance ID: DTXSID60883376
• Nikkaji Number: J59.695G
• Wikipedia: Tosyl_phenylalanyl_chloromethyl_ketone
• Wikidata: Q7827912
• Metabolomics Workbench ID: 53488
• ChEMBL ID: CHEMBL60718
• Mol file: 402-71-1.mol

Synonyms:Chloromethane, Tosylphenylalanyl;Chloromethyl Ketone, Tosylphenylalanyl;Chlorophenyltosylamidobutanone;Ketone, Tosylphenylalanyl Chloromethyl;Tosylphenylalanyl Chloromethane;Tosylphenylalanyl Chloromethyl Ketone;TPCK

Chemical Property of Tosylphenylalanyl chloromethyl ketone

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.63E-10mmHg at 25°C
• Melting Point: 106-108 °C(lit.)
• Refractive Index: 1.582
• Boiling Point: 509.9 °C at 760 mmHg
• PKA: 8.71±0.50(Predicted)
• Flash Point: 262.2 °C
• PSA: 71.62000
• Density: 1.278 g/cm³
• LogP: 4.16420
• Storage Temp.: ?20°C
• Solubility.: DMSO: >10?mg/mL stable for several months at 4°C.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 351.0695923
• Heavy Atom Count: 23
• Complexity: 475

Purity/Quality:

97% ^*data from raw suppliers

N-Tosyl-L-phenylalanine chloromethyl ketone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(CC2=CC=CC=C2)C(=O)CCl
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CC2=CC=CC=C2)C(=O)CCl
• General Description: **Conclusion:** Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-, also known as N-Tosyl-L-Phenylalanine chloromethyl ketone (TPCK), is an irreversible serine protease inhibitor. It can be synthesized via a safer and practical route by tosylating L-phenylalanine, forming a 4-nitrophenyl ester, and reacting it with dimethylsulfoxonium methylide, followed by treatment with lithium chloride and methanesulfonic acid. This method avoids hazardous reagents like diazomethane and achieves a 36% overall yield.

Refernces

Facile preparation of N-Tosyl-L-Phenylalanine chloromethyl ketone

10.2174/157017809790443005

The study presents a new method for preparing N-tosyl-L-phenylalanine chloromethyl ketone (TPCK), an irreversible serine protease inhibitor, without using toxic and explosive diazomethane. L-Phenylalanine is first tosylated to form N-tosyl-L-phenylalanine, which is then converted into its 4-nitrophenyl ester using DCC and DMAP. This ester reacts with dimethylsulfoxonium methylide, generated from trimethylsulfoxonium iodide and potassium tert-butoxide, to form a sulfur ylide. The sulfur ylide is subsequently treated with lithium chloride and methanesulfonic acid to produce the chloroketone, TPCK. This method achieves an overall yield of 36% and avoids the use of hazardous diazomethane, providing a safer and practical synthesis route.