(1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine

CAS: 167316-27-0

Ref. TR-T535930

Product Information

• Name: (1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine
• Synonyms: N-[(1S,2S)-2-Amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide, [S-(R*,R*)]-N-(2-Amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide, (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylene-1,2-diamine, (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine, (1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine, (1S,2S)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine, (1S,2S)-N-(p-Tolylsulfonyl)-1,2-diphenylethylenediamine, ((1S,2S)-N'-[(4-Methylphenyl)sulfonyl]-1,2-diphenyl-1,2-ethanediamine, (S,S)-N-p-Toluenesulfonyl-1,2-diphenylethylenediamine, (S,S)-TsDPEN, N-Tosyl-(1S,2S)-1,2-diphenylethylenediamine, N-[(1S,2S)-2-Amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide, N-((1S,2S)-2-amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide, (1S,2S)-2-{[(4-methylphenyl)sulfonyl]amino}-1,2-diphenylethanaminium

Description

Applications (1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine is used as a catalyst in the synthesis of keramamine C, a carboline alkaloid that is isolated from the Okinawan sponge Amphimedon sp. (1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine is also used as a catalyst in the synthesis of Tolvaptan (T536650), a selective oral vasopressin V2-receptor agonist that is used to treat hyponatremia.
References Hu, J., et al.: Alkaloid. New York-Acad. Press, 60, 207 (2003); Ishiyama, H., et al.: Heterocycles, 86, 1009 (2012); Schrier, R., et al.: New Engl. J. Med., 355, 2099 (2006); Yin, L., et al.: Tetrahedron-Assymetr., 21, 2390 (2010)

• Brand: TRC

Chemical properties

• Molecular weight: 366.48
• Formula: C₂₁H₂₂N₂O₂S
• Color/Form: Neat
• InChI: InChI=1S/C21H22N2O2S/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17/h2-15,20-21,23H,22H2,1H3/t20-,21-/m0/s1
• InChI key: InChIKey=UOPFIWYXBIHPIP-SFTDATJTSA-N
• SMILES: Cc1ccc(S(=O)(=O)N[C@@H](c2ccccc2)[C@@H](N)c2ccccc2)cc1