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

White to slightly yellow crystalline powder

Synthesis of Compound 2009: To a 2-L, three-neck, round-bottom flask equipped with a temperature probe, magnetic stir bar, nitrogen inlet, and addition funnel were added (lS, 2S)-(-)-l, 2-diphenylethylenediamine (20 g, 0.094 mol) and dichloromethane (160 mL). The mixture was cooled to 0-3 The procedure is the same as in Example 1, Except that (1S, 2S) -1, 2-diphenylethylenediamine (3.0 g, 14.1 mmol)Added to 50mLDCM, After stirring and dissolving, A 15 mL aqueous solution of 2N NaOH was added, Cooling to 0 , A solution of p-toluenesulfonyl chloride (2.65 g, 14.1 mmol)In dichloromethane (30 mL)After maintaining the reaction at 0 ° C for 1 hour, The temperature was raised to room temperature for 2 hours, HPLC detection reaction ended.The reaction solution was poured into saturated sodium chloride solution (30 mL)Stir for 10 minutes, After stratification, The aqueous phase was extracted once with DCM (30 mL)Combine organic phase, dry, The dichloromethane was removed by distillation under reduced pressure, Get crude.Recrystallization from petroleum ether / ethyl acetate system gave yellow solid Compound I (4.48 g, 82.3percent)A solution of N-[(1 S, 2S)-2-amino- 1 , 2-diphenylethyl]-4-methylbenzene- 1-sulfonamide (S, S-Ts-DPEN) (1.09 g, 3.00 mmol), Et3N (0.90 mL, 6.47 mmol), and [RuC12(hexamethylbenzene)]2 (1.00 g, 1.50 mmol) in DCM (40 mL) was stirred for 5 h at 25 C. The resulting mixture was concentrated under vacuum. The residue was purified by silica gel chromatography (eluting with 1:10 MeOHIDCM) to afford RuC1-(S, S)-Ts- DPEN(hexamethylbenzene) as a red solid.Synthesis of Compound 2009: To a 2-L, three-neck, round-bottom flask equipped with a temperature probe, magnetic stir bar, nitrogen inlet, and addition funnel were added (lS, 2S)-(-)-l, 2-diphenylethylenediamine (20 g, 0.094 mol) and dichloromethane (160 mL). The mixture was cooled to 0-3 0C and a 1 M solution of sodium hydroxide (160 mL) was added dropwise while maintaining the temperature below 5 0C. To this mixture was added a solution of toluenesulfonyl chloride (17.9 g, 0.094 mol) in dichloromethane (320 mL) dropwise over a 2-h period. The biphasic mixture was stirred at 0-5 0C for an additional 1 h and the reaction was deemed complete by TLC (50% EtO Ac/heptane, UV). Phases were separated and the organic phase was washed with water (2 x 320 mL) and brine (320 mL), dried over sodium sulfate and concentrated to a crude solid. The solid was dissolved in toluene (200 mL) at 70-80 0C and heptane (300 mL) was added portionwise while maintaining this temperature. The resulting slurry was cooled and stirred at 20-25 0C for 1 h and then cooled and stirred at 0-5 0C for 10 min. The solids were filtered and washed with a 50% solution of toluene in heptane (3 x 1 bed volume) to give compound 2009 (30.24 g, 88%) as a white powder.The procedure is the same as in Example 1, Except that (1S, 2S) -1, 2-diphenylethylenediamine (3.0 g, 14.1 mmol)Added to 50mLDCM, After stirring and dissolving, A 15 mL aqueous solution of 2N NaOH was added, Cooling to 0 , A solution of p-toluenesulfonyl chloride (2.65 g, 14.1 mmol)In dichloromethane (30 mL)After maintaining the reaction at 0 C for 1 hour, The temperature was raised to room temperature for 2 hours, HPLC detection reaction ended.The reaction solution was poured into saturated sodium chloride solution (30 mL)Stir for 10 minutes, After stratification, The aqueous phase was extracted once with DCM (30 mL)Combine organic phase, dry, The dichloromethane was removed by distillation under reduced pressure, Get crude.Recrystallization from petroleum ether / ethyl acetate system gave yellow solid Compound I (4.48 g, 82.3%)

Molecular Weight:366.5
XLogP3:3.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:366.14019912
Monoisotopic Mass:366.14019912
Topological Polar Surface Area:80.6
Heavy Atom Count:26
Complexity:511
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes