CAS 167316-27-0 (S,S)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide

Synonyms

ST2402122; (1S,2S)-TSDPEN; C21H22N2O2S; EBD12781; AJ-48759; CBiol_000203; (S,S)-TSDPEN; CTK3J8236; BBL102186; (1s,2s)-(+)-n-(4-toluenesulphonyl)-1,2-diphenylethylenediamine;

IUPAC Name

N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide;

Molecular Weight

366.479g/mol

Molecular Formula

C21H22N2O2S;

Canonical SMILES

CC1=CC=C(C=C1)S(=O)(=O)NC(C2=CC=CC=C2)C(C3=CC=CC=C3)N;

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

UOPFIWYXBIHPIP-SFTDATJTSA-N;

Complexity

511

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

366.14g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

366.14g/mol

Rotatable Bond Count

Topological Polar Surface Area

80.6A^2

Application

(S,S)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide serves as a versatile catalyst in chemical synthesis, primarily offering its utility in the production of keramamine C, a carboline alkaloid extracted from the Okinawan sponge Amphimedon sp., and Tolvaptan, a selective oral vasopressin V2-receptor agonist employed to treat hyponatremia. As a chiral diamine ligand, it supports cooperative metal-Brønsted acid catalysis for greener and more efficient reductive amination under hydrogen gas. This product reflects our commitment to Greener Chemistry, aiming to enhance catalytic efficiency while adhering to the principles that promote environmentally friendly chemical practices.

February 19, 2025

Exceptional Catalyst for Research Applications

(S,S)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide was vital in synthesizing keramamine C and Tolvaptan. Its efficiency as a chiral diamine ligand made our asymmetric reductive amination process significantly greener and more efficient.