(1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine

Base Information

• Chemical Name: (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine
• CAS No.: 167316-27-0
• Molecular Formula: C21H22N2O2S
• Molecular Weight: 366.484
• Hs Code.: 29242990
• European Community (EC) Number: 626-353-6
• DSSTox Substance ID: DTXSID30425045
• Wikidata: Q72509253
• Mol file: 167316-27-0.mol

Synonyms:167316-27-0;(1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine;(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine;(S,S)-TSDPEN;N-((1S,2S)-2-amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide;(1s,2s)-n-(4-toluenesulfonyl)-1,2-diphenylethylene-1,2-diamine;N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide;(1s,2s)-(-)-n-p-tosyl-1,2-diphenylethylenediamine;Benzenesulfonamide, N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methyl-;(S,S)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide;MFCD03095684;(1S,2s)-n-(4-toluenesulfonyl)-1,2-diphenylethylenediamine;(S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethylenediamine;224454-16-4;(1S, 2S)-(+)-N-(4-Toluene sulfonyl)1,2-diphenyl-1,2-ethane diamine;(IS,2S)-TsDPEN;CBiol_000203;(1S,2S)-TSDPEN;SCHEMBL130104;AMY207;DTXSID30425045;UOPFIWYXBIHPIP-SFTDATJTSA-N;BBL102186;ICCB2_000203;N-[(1S,2S)-2-amino-1,2-diphenyl-ethyl]-4-methyl-benzenesulfonamide;STL555985;AKOS015854024;AC-3418;SC11720;AS-11923;BP-12256;A3707;CS-0016225;H10868;N-Tosyl-(1R,2R)-1,2-dipenyl ethylenediamine;W18862;(1S,2S)-N-p-Tosyl-1,2-diphenylethylenediamine;AS-813/11524155;J-010354;J-523290;W-201261;(1s, 2s)-(+)-n-p-tosyl-1,2-diphenylethylenediamine;(1s,2s)-(+)-n-p-tosyl-1,2-diphenylethylene diamine;N-TOSYL-(1S,2S)-1,2-DIPHENYL ETHYLENEDIAMINE;(1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine;(S,S)-N-(p-toluenesulfonyl)-1,2-diphenylethylendiamine;(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine, 98%;(1S,2S)-(+)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine;(1S,2S)-(+)-N-(4-toluene-sulfonyl)-1,2-diphenylethylenediamine;N-((1S,2S)-2-Amno-1,2-dphenylethyl)-4-methylbenzenesulfonamde;N-[(1S,2S)-2-Amino-1,2-diphenylethyl]-4- methylbenzenesulfonamide;N-[(1S,2S)-2-Amino-1,2-diphenylethyl]-4-methylbenzene-1-sulfonamide

Chemical Property of (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine

Chemical Property:

• Appearance/Colour: White to slightly yellow crystalline powder
• Vapor Pressure: 1.28E-11mmHg at 25°C
• Melting Point: 128-131 °C(lit.)
• Refractive Index: 30 ° (C=1, CHCl3)
• Boiling Point: 537.3 °C at 760 mmHg
• PKA: 10.76±0.50(Predicted)
• Flash Point: 278.8 °C
• PSA: 80.57000
• Density: 1.224 g/cm³
• LogP: 5.88660
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Solubility in hot Acetonitrile (almost transparency).
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 366.14019912
• Heavy Atom Count: 26
• Complexity: 511

Purity/Quality:

99% ^*data from raw suppliers

(1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(C2=CC=CC=C2)C(C3=CC=CC=C3)N
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](C2=CC=CC=C2)[C@H](C3=CC=CC=C3)N
• Uses: (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.

Technology Process of (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine

There total 5 articles about (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine 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: 95.5%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + p-toluenesulfonyl chloride (98-59-9) → (1S,2S)-N,N'-bis((4-methylphenyl)sulfonyl)-1,2-diphenylethane-1,2-diamine (170709-41-8) + N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide (167316-27-0)

Guidance literature:

With sodium hydroxide; water; In dichloromethane; at 0 ℃; for 2h; Product distribution / selectivity;

Reference yield: 95.0%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + p-toluenesulfonyl chloride (98-59-9) → N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide (167316-27-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 12h; Cooling with ice;

DOI:10.1039/c0ob00757a

Reference yield: 51.0%

benzyl 2,3,6-trideoxy-β-L-hex-2-enopyranosid-4-ulose → (2S,3R,6S)-6-(benzyloxy)-2-methyltetrahydro-2H-pyran-3-ol + N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide (167316-27-0)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium formate; N-tosylethylenediamine; at 40 ℃; stereoselective reaction;

DOI:10.1039/c5cc07787g

upstream raw materials:

(S,S)-1,2-diphenyl-1,2-diaminoethane

p-toluenesulfonyl chloride

(1S,2S)-2-amino-1,2-diphenylethanol

Downstream raw materials:

(-)-(S)-5-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-8-hydroxy-1-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepin-4-one

(1S,2S)-N-(1,2-diphenyl-2-(piperidin-1-yl)ethyl)-4-methyl-benzenesulfonamide

4-methyl-N-((1S,2S)-2-(4-methylbenzylamino)-1,2-diphenylethyl)benzenesulfonamide

C₂₈H₂₈N₂O₂S

Refernces

• 1、 Santos, Leonardo S.,Pilli, Ronaldo A.,Rawal, Viresh H.. "Enantioselective Total Syntheses of (+)-Arborescidine A, (-)-Arborescidine B, and (-)-Arborescidine C". . p. 1283 - 1289. Retrieved 2004.
• 2、 Song, Wangze,Zhao, Yu,Lynch, John C.,Kim, Hyunjin,Tang, Weiping. "Divergent de novo synthesis of all eight stereoisomers of 2,3,6-trideoxyhexopyranosides and their oligomers". . p. 17475 - 17478. Retrieved 2015/12/08.
• 3、 Li, Wenjun,Wu, Wenbin,Yu, Feng,Huang, Huicai,Liang, Xinmiao,Ye, Jinxing. "Catalytic asymmetric Michael addition with curcumin derivative". supporting information; experimental part. p. 2505 - 2511. Retrieved 2011/05/06.