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

Melting point:

128-131 °C (lit.)

alpha 

61.5 º (C=1, CH2Cl2)

Boiling point:

537.3±60.0 °C(Predicted)

Density 

1.1440 (rough estimate)

refractive index 

30 ° (C=1, CHCl3)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Solubility in hot Acetonitrile (almost transparency).

pka

10.76±0.50(Predicted)

form 

crystal

color 

white

optical activity

[α]20/D +35°, c = 1 in chloroform

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

InChIKey

UOPFIWYXBIHPIP-SFTDATJTSA-N

SMILES

C1(S(N[C@@H](C2=CC=CC=C2)[C@@H](N)C2=CC=CC=C2)(=O)=O)=CC=C(C)C=C1

CAS DataBase Reference

167316-27-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29242990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

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

Chemical Properties

White to slightly yellow crystalline powder

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.

Uses

Chiral diamine ligand for cooperative metal-Bronsted acid catalyzed greener reductive amination using hydrogen gas.

Metal-Br?nsted Acid Cooperative Catalysis for Asymmetric Reductive Amination

General Description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Synthesis

Synthesis of Compound 2009: To a 2 L three-necked round-bottomed flask equipped with a temperature probe, magnetic stirring bar, nitrogen inlet, and constant-pressure dropping funnel was added (1S,2S)-1,2-diphenylethylenediamine (20 g, 0.094 mol) and dichloromethane (160 mL). The reaction mixture was cooled to 0-3 °C and 1 M sodium hydroxide solution (160 mL) was added slowly and dropwise while keeping the temperature below 5 °C. Subsequently, a solution of dichloromethane (320 mL) of p-toluenesulfonyl chloride (17.9 g, 0.094 mol) was added dropwise to the reaction system over a period of 2 hours. The biphasic reaction mixture was continued to be stirred at 0-5 °C for 1 h. Completion of the reaction was confirmed by thin layer chromatography (TLC, 50% ethyl acetate/heptane, UV detection). After completion of the reaction, the organic and aqueous phases were separated, and the organic phase was washed sequentially with water (2×320 mL) and saturated saline (320 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was dissolved in toluene (200 mL) at 70-80 °C, maintained at this temperature, and heptane (300 mL) was added in batches. The resulting slurry was cooled to 20-25 °C and stirred for 1 hour, then further cooled to 0-5 °C and stirred for 10 minutes. The solid was collected by filtration and washed with a heptane solution of 50% toluene (3 x 1 bed volume) to give compound 2009 (30.24 g, 88% yield) as a white powder.

References

[1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2505 - 2511
[2] Journal of Organic Chemistry, 2004, vol. 69, # 4, p. 1283 - 1289
[3] Patent: WO2010/120719, 2010, A1. Location in patent: Page/Page column 194; 196-197
[4] Patent: CN106496099, 2017, A. Location in patent: Paragraph 0033; 0034; 0035; 0048; 0049
[5] Organic Syntheses, 2005, vol. 82, p. 10 - 17

(1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine(167316-27-0)Related Product Information

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