Hydroxylamine → HCID 71748115, compound

Participants

Reaction Steps

Solid K2CO3 (7.5 mg, 0.052 mmol) was added to a solution of (R)-1-{(S)-2-[2-{(tert-butoxycarbonylamino)methyl}-5-chlorobenzylcarbamoyl]-piperidin-1-yl}-3,3-dimethyl-1-oxobutan-2-yl acetate (0.14 g, 0.26 mmol) in MeOH (5 mL) and the resulting mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with EtOAc (50 mL) and washed sequentially with 0.1 N 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 provide the intermediate BOC protected amino alcohol (0.12 g, crude) as an off-white solid. The crude intermediate was dissolved in CH2Cl2 (2 mL) then trifluoroacetic acid (0.5 mL, 27.20 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then volatile byproducts were removed under reduced pressure residue. 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: 7.36-7.46 (m, 3H), 4.99-5.08 (m, 1H), 4.01-4.51 (m, 6H), 3.36-3.37 (m, 1H), 2.15-2.21 (m, 1H), 1.64-1.68 (m, 3H), 1.39-1.54 (m, 2H), 0.98 (s, 9H).

Provenance & Evidence