Trifluoroacetic acid → HCID 60150642, compound

Participants

Reaction Steps

Solid K2CO3 (5.8 mg, 0.042 mmol) was added to the solution of (R)-1-{(R)-3-[2-{(tert-Butoxycarbonylamino)methyl}-5-chlorobenzylcarbamoyl]thiomorpholino)-3,3-dimethyl-1-oxo-butan-2-yl acetate (0.12 g, 0.21 mmol) in MeOH (5 mL) and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with EtOAc (50 mL) and washed with 0.1M aqueous HCl (20 mL), water (2×20 mL), and brine solution (20 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile/water) to afford the intermediate BOC-protected alcohol as an off-white solid (0.092 g, crude). The crude intermediate was dissolved in CH2Cl2 (3 mL) then trifluoroacetic acid (1.0 mL, 13.42 mmol) was added and the resulting mixture was stirred at room temperature for 2 h. Volatile byproducts were removed under vacuum and the residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile:water) to afford the title compound as a white solid. 1H NMR (MeOD 400 MHZ) (δ) ppm: 7.41 (s, 1H); 7.39-7.35 (m, 2H); 5.28 (t, J=4.4 Hz, 1H); 4.54-4.38 (m, 3H); 4.28-4.21 (m, 3H); 3.61-3.54 (m, 1H); 3.18-3.12 (m, 1H); 2.93-2.88 (m, 1H); 2.82-2.75 (m, 1H); 2.62-2.59 (m, 1H), 0.98 (m, 9H).

Provenance & Evidence