Trifluoroacetic acid → HCID 67271886, compound

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).

1. concentrationThe mixture was then concentrated in vacuo with addition of toluene
2. additionThe residue was added 1N aqueous HCl solution (50 mL)
3. washwashed with diethyl ether (80 mL)
4. washThe diethyl ether layer was washed with 1N aqueous HCl solution again
5. extractionextracted with ethyl acetate
6. washThe organic phase was washed with H2O
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo

ORD record

ord-6d632a25a6fc4c6ab16fd7ecc62801c0

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902218B2