N-(p-Toluenesulfonyl)-L-phenylalanine

Base Information

• Chemical Name: N-(p-Toluenesulfonyl)-L-phenylalanine
• CAS No.: 13505-32-3
• Molecular Formula: C16H17NO4S
• Molecular Weight: 319.381
• Hs Code.: 29224999
• Nikkaji Number: J534.179E
• ChEMBL ID: CHEMBL3275993
• Mol file: 13505-32-3.mol

Synonyms:N-tosyl-(S)-phenylalanine

Chemical Property of N-(p-Toluenesulfonyl)-L-phenylalanine

Chemical Property:

• Vapor Pressure: 1.52E-11mmHg at 25°C
• Melting Point: 165 °C
• Refractive Index: -2.8 ° (C=4.5, Acetone)
• Boiling Point: 517.7°Cat760mmHg
• PKA: 3.31±0.10(Predicted)
• Flash Point: 266.9°C
• PSA: 91.85000
• Density: 1.303g/cm³
• LogP: 3.44090
• Storage Temp.: Store at RT.
• Solubility.: almost transparency in hot EtOH
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 319.08782920
• Heavy Atom Count: 22
• Complexity: 457

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Tosyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(CC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O

Technology Process of N-(p-Toluenesulfonyl)-L-phenylalanine

There total 8 articles about N-(p-Toluenesulfonyl)-L-phenylalanine 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: 100.0%

N-(p-toluenesulfonyl) phenylalanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl) methyl ester (918886-05-2) → N-tosyl-(S)-phenylalanine (13505-32-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 0 ℃; for 9h;

DOI:10.1016/j.tet.2006.09.085

Reference yield: 99.93%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl-(S)-phenylalanine (13505-32-3)

Guidance literature:

With sodium carbonate; In water; for 5h;

DOI:10.1016/j.ejmech.2017.04.029

Reference yield: 90.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + toluene-4-sulfonic acid (104-15-4) → N-tosyl-(S)-phenylalanine (13505-32-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 2h; pH=> 8; Cooling with ice;

DOI:10.1016/j.ejmech.2020.112160

upstream raw materials:

1-Octyn-3-ol

N-(p-toluenesulfonyl)-L-phenylalanyl chloride

7-(N-tosyl-L-phenylalanyl)amino-4-nitrobenzo-2-oxa-1,3-diazole

L-phenylalanine

Downstream raw materials:

N-(p-toluenesulfonyl)-L-phenylalanyl chloride

(S)-3-Phenyl-N-pyrimidin-2-yl-2-(toluene-4-sulfonylamino)-propionamide

L-phenylalanine

D-(R)-phenylalanine

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.

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