Acetyl chloride → HCID 21187761, compound

Participants

Reaction Steps

To a solution of 2-(2-aminoethylamino)ethanol (1.15 g, 11 mmol, 1.10 equiv) in 50 mL MeOH at 0° C. was slowly added ethyl trifluoroacetate (1.42 g, 10 mmol, 1.00 equiv). The mixture was stirred at room temperature for 5 hours. Solvents were then removed, and the residue was dissolved in 50 mL methylene chloride. Triethylamine (1.52 g, 15 mmol) was added followed by acetyl chloride (0.94 g, 12 mmol, 1.20 equiv). Removal of solvent yielded N-acetyl-N-(2-trifluoroacetylaminoethyl)-(2′-hydroxyethyl)amine (crude) as a white solid. This crude product was subjected to a series of reactions similar to those for SBR-11-4416. 0.60 g final product was isolated as a white solid after HPLC purification. 1H NMR (CDCl3, ppm): 8.47(d, 2H), 7.99 (brs, 2H), 7.14-7.35 (m, 10H), 5.20 (s, 1H), 2.96-3.56 (m, 12H), 2.18 (s, 3H). MS: 482.24 (calc'd); 483.5 (M+1).

Provenance & Evidence