Trifluoroacetic acid → HCID 118307244, compound

To a solution of compound I2 (87.0 mg, 0.240 mmol) in anhydrous methylene chloride (3 mL) was added trifluoroacetic acid (3 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 24 h. After this time, the reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in methylene chloride (50 mL), washed with saturated aqueous sodium bicarbonate (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with methylene chloride to methanol/methylene chloride (1:19) to afford compound I3 as a yellow solid (38 mg, 60%): 1H NMR (500 MHz, CDCl3) δ 6.17 (bs, 2H), 3.48 (s, 2H), 2.99-2.96 (m, 2H), 2.82-2.79 (m, 2H), 2.62 (q, J=7.0 Hz, 2H), 2.39 (s, 3H), 1.18 (t, J=7.0 Hz, 3H). MS (M+H) 265.

1. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure
2. dissolutionThe resulting residue was dissolved in methylene chloride (50 mL)
3. washwashed with saturated aqueous sodium bicarbonate (50 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by flash column chromatography on silica gel eluting with methylene chloride to methanol/methylene chloride (1:19)

ORD record

ord-f37fc199c40f46979b31d996a2094ac3

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09416141B2