Luna c18

Example 23

To 23c-int (0.4 g) in THF (10 mL)/H₂O (10 mL) was added LiOH. H₂O (0.16 g, 3.78 mmol). The mixture was stirred for 2 h at 30° C. then was concentrated and purified by prep-HPLC to give Example 23.

HPLC purification conditions: Gilson 281 semi-preparative HPLC system; Mobile phase A: TFA/H₂O=0.075% v/v; B: AcN (gradient % B at T=0: 10%; at T=12 min: 30%); Column: Luna C18 100×30 5 u; Flow rate: 20 mL/min; Monitor wavelength: 220 & 254 nm.

¹H NMR (400 MHz, CHLOROFORM-d): δ ppm 2.03-1.97 (m, 2H) 2.59-2.49 (m, 3H) 3.21 (t, J=10.4 Hz, 2H) 3.89 (d, J=5.2 Hz, 3H) 5.12-5.07 (m, 1H) 5.42 (s, 1H) 6.38 (d, J=7.6 Hz, 1H) 6.69-6.63 (m, 2H) 6.77 (d, J=8.8 Hz, 2H) 7.15 (d, J=8.8 Hz, 2H) 7.28-7.22 (m, 3H) 7.79-7.74 (m, 2H) 9.67 (s, 1H); LCMS (ESI+): m/z=514.0 (M+H)⁺, RT: 2.2 min; HPLC purity: 95.3%, RT: 6.2 min; Chiral SFC purity: 100%, ee value: 100%, RT: 3.4 min.

Example 23

To 23c-int (0.4 g) in THF (10 mL)/H₂O (10 mL) was added LiOH. H₂O (0.16 g, 3.78 mmol). The mixture was stirred for 2 h at 30° C. then was concentrated and purified by prep-HPLC to give Example 23.

HPLC purification conditions: Gilson 281 semi-preparative HPLC system; Mobile phase A: TFA/H₂O=0.075% v/v; B: AcN (gradient % B at T=0: 10%; at T=12 min: 30%); Column: Luna C18 100×30 5 u; Flow rate: 20 mL/min; Monitor wavelength: 220 & 254 nm.

¹H NMR (400 MHz, CHLOROFORM-d): δ ppm 2.03-1.97 (m, 2H) 2.59-2.49 (m, 3H) 3.21 (t, J=10.4 Hz, 2H) 3.89 (d, J=5.2 Hz, 3H) 5.12-5.07 (m, 1H) 5.42 (s, 1H) 6.38 (d, J=7.6 Hz, 1H) 6.69-6.63 (m, 2H) 6.77 (d, J=8.8 Hz, 2H) 7.15 (d, J=8.8 Hz, 2H) 7.28-7.22 (m, 3H) 7.79-7.74 (m, 2H) 9.67 (s, 1H); LCMS (ESI+): m/z=514.0 (M+H)⁺, RT: 2.2 min; HPLC purity: 95.3%, RT: 6.2 min; Chiral SFC purity: 100%, ee value: 100%, RT: 3.4 min.