Triethylamine → N-[(1R,2R)-2-Amino-1,2-diphenylethyl]-2,4,6-tris(1-methylethyl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

(1R,2R)-1,2-Diphenyl-ethane-1,2-diamine (1.0 g) was dissolved in dichloromethane (20 mL), and then triethylamine (0.66 mL) added and the mixture was cooled to 5° C. (internal). 2,4,6-Triisopropyl-benzenesulfonyl chloride (1.21 g) was dissolved in dichloromethane (10 mL) and then added to the diamine mixture over 30 minutes, while maintaining the temperature between 7-10 ° C. The cooling bath was removed and the resulting mixture was stirred at 25° C. for 4 hours and the solvent was evaporated. The resulting residue was suspended in hexanes (100 mL) and washed with warm water (42° C., 3×100 mL). The hexane layer was separated, dried over Na2SO4, filtered, and evaporated to provide the product (1.85 g). 1HNMR (400 MHz, CDCl3): δ(ppm) 7.20-7.15 (m, 3H), 7.05-6.94 (m, 7H), 6.84-6.80 (m, 2H), 6.09 (br-s,1H), 4.49 (d, 1H), 3.99-3.91 (m, 3H), 2.87-2.79 (m, 1H), 1.21 (d, 6H), 1.17 (d, 6H), 1.08 (d, 6H). LC/MS: 479 (m/z).

Provenance & Evidence