N-(P-TOLUENESULFONYL)-L-PHENYLALANINE Chemical Properties

Melting point:

165 °C

Boiling point:

517.7±60.0 °C(Predicted)

Density 

1.303±0.06 g/cm3(Predicted)

refractive index 

-2.8 ° (C=4.5, Acetone)

storage temp. 

Sealed in dry,Room Temperature

solubility 

almost transparency in hot EtOH

form 

powder to crystal

pka

3.31±0.10(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C16H17NO4S/c1-12-7-9-14(10-8-12)22(20,21)17-15(16(18)19)11-13-5-3-2-4-6-13/h2-10,15,17H,11H2,1H3,(H,18,19)/t15-/m0/s1

InChIKey

CGRCVIZBNRUWLY-HNNXBMFYSA-N

SMILES

C(O)(=O)[C@H](CC1=CC=CC=C1)NS(C1=CC=C(C)C=C1)(=O)=O

CAS DataBase Reference

13505-32-3(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HazardClass 

IRRITANT

HS Code 

29224999

N-(P-TOLUENESULFONYL)-L-PHENYLALANINE Usage And Synthesis

Chemical Properties

White to off-white solid

Synthesis

GENERAL STEPS: Sodium carbonate (Na2CO3, 1.590 g, 15 mmol) was added dropwise to an aqueous solution (15 mL) of L-phenylalanine (12.5 mmol) under continuous stirring conditions until complete dissolution. Subsequently, the reaction system was cooled to -5°C and p-toluenesulfonyl chloride (15 mmol) was slowly added in four portions over 1 hour. The reaction mixture was continued to be stirred at room temperature for 4 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent was methanol/dichloromethane, 1:9). Upon completion of the reaction, the mixture was acidified with 20% aqueous hydrochloric acid to pH 2. The precipitated solid was collected by diafiltration and washed with pH 2.2 buffer. Finally, the purified product (S)-2-(4-methylphenylsulfonamido)-3-phenylpropionic acid was placed in a desiccator and dried using fused silica gel as desiccant.

References

[1] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 349 - 369
[2] PLoS ONE, 2018, vol. 13, # 1,
[3] RSC Advances, 2015, vol. 5, # 24, p. 18751 - 18760
[4] European Journal of Organic Chemistry, 2005, # 5, p. 934 - 938
[5] Journal of Organic Chemistry, 2012, vol. 77, # 9, p. 4375 - 4384

N-(P-TOLUENESULFONYL)-L-PHENYLALANINE(13505-32-3)Related Product Information

• TOS-LYS(BOC)-OH
• N-(p-Tolylsulphonyl)-L-glutamic acid
• TOS-PRO-OH
• N-P-TOSYLGLYCINE
• SALOR-INT L173339-1EA
• TOS-ALA-OH
• P-TOLUENESULFONYL-L-PHENYLALANINE CHLOROMETHYL KETONE
• P-TOLUENESULFONYL-L-PHENYLALANINE CHLOROMETHYL KETONE,NALPHA-(4-Toluenesulfonyl)-L-phenylalanine chloromethyl ketone
• N-Propyl-P-Toluenesulfonamide
• N-phenethylmethanesulphonamide
• (S)-(-)-N-[1-(HYDROXYMETHYL)-2-PHENYLETHYL]-4-METHYLBENZENESULFONAMIDE
• N-(2-hydroxyethyl)benzenesulfonamide
• 2-(TOLUENE-4-SULFONYLAMINO)-PROPIONIC ACID
• N-(P-TOLUENESULFONYL)-L-PHENYLALANINE
• BSMOC-TYROSINE
• BSMOC-PHENYLALANINE