Trifluoroacetic acid → HCID 67271886, compound

Participants

Reaction Steps

A solution of (S)-tert-butyl 3-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (step E (1), 550 mg) in CH2Cl2 (20 mL) was treated with TFA (10 mL). This reaction mixture was stirred at rt for 2 h. The mixture was then concentrated in vacuo with addition of toluene. The residue was added 1N aqueous HCl solution (50 mL) and washed with diethyl ether (80 mL). The diethyl ether layer was washed with 1N aqueous HCl solution again. The combined aqueous layers were neutralized with 50% aqueous NaOH solution, extracted with ethyl acetate. The organic phase was washed with H2O, and dried (Na2SO4), and concentrated in vacuo to give 350 mg (81% yield) of the title compound: 1H NMR (CDCl3, 500 MHz) δ 2.23 (1H, brd s), 2.72 (1H, dd, J=5, 15 Hz), 2.88 (1H, dd, J=10, 15 Hz), 3.02 (1H, m), 3.10 (1H, dd, J=10, 15 Hz), 3.22 (1H, m), 4.06 (2H, s), 4.12 (1H, m), 4.63 (1H, m), 5.64 (1H, s), 6.69-6.77 (3H, m), 7.04 (1H, t, J=5 Hz), 7.08 (1H, t, J=5 Hz), 7.12-7.15 (2H, m).

Provenance & Evidence