Hydrochloric Acid → HCID 11508820, compound

To a solution of Example 18A (100 mg) in tetrahydrofuran (0.5 mL) and ethanol (0.5 mL) was added 2 M NaOH (1 mL) and the resulting mixture was stirred at room temperature for 16 hours. The mixture was adjusted to a pH 2-3 by the addition of 1 M HCl, extracted with ethyl acetate (3×15 mL) and the combined organic layers washed with brine (15 mL), dried (Na2SO4), filtered and concentrated to provide a white solid which was processed as described in Example 18 to provide the titled compound as a pale yellow solid. MS (ESI) m/e 364 (M+H)+; 1H NMR (500 MHz, CD3OD) δ ppm 1.82 (m, 1H), 2.74 (m, 1H), 2.83 (m, 1H), 3.09 (m, 1H), 3.17 (q, 1H), 3.24 (dd, 1H), 3.33 (m, 1H), 3.55 (m, 2H), 3.64 (m, 1H), 3.75 (m, 1H), 3.88 (m, 1H), 4.52 (m, 1H), 4.66 (m, 2H), 7.60 (m, 1H), 8.06 (t, 1H), 8.20 (d, 1H), 8.49 (m, 1H).

1. extractionextracted with ethyl acetate (3×15 mL)
2. washthe combined organic layers washed with brine (15 mL)
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customto provide a white solid which

ORD record

ord-0ae46eb0787346aba66687c06ad1a007

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348346B2