Trifluoroacetic acid → HCID 68433377, compound

Participants

Reaction Steps

To a solution of tert-butyl 2-(benzyloxy)-1-{[(bromoacetyl)(4-fluorobenzyl)amino]methyl}ethylcarbamate (2.79 g, 5.47 mmol) in CH2Cl2 (28 mL) was added trifluoroacetic acid (10 ml). The reaction was stirred at ambient temperature under inert atmosphere for 2 h and then concentrated in vacuo, azeotroping the residual oil with CHCl3. The resulting residue was dissolved in CH2Cl2 (100 mL) and treated with Hünig's base (10 mL). The solution was stirred at ambient temperature under inert atmosphere for 18 h. The solvent was removed in vacuo, and the remaining residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. Purification by silica gel chromatography (EtOAc to 10% MeOH/EtOAc) afforded the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.37-7.22 (m, 7H), 7.04-6.98 (m, 2H), 4.64 (d, J=14.8 Hz, 1H), 4.49-4.44 (m, 3H), 3.63 (dd, J=17.6, 41.2 Hz, 2H), 3.47 (dd, J=4.0, 9.6 Hz, 1H), 3.40 (dd, J=6.4, 9.2 Hz, 1H), 3.22-3.16 (m, 1H), 3.10-3.06 (m, 2H), 1.71 (br s, 1H). ES MS (M+1)=329.3.

Provenance & Evidence