Pyridine → Ethyl 2-(2-cyanoacetamido)-2-methyl-4-oxo-4-p-tolylbutanoate

To a solution of Intermediate 3C (2.192 g, 21.18 mmol) in DCM (30 mL) under argon was added Intermediate 102C (1.2 g, 4.81 mmol), pyridine (0.779 mL, 9.63 mmol) and DMAP (0.059 g, 0.481 mmol). The reaction mixture was stirred at rt for 1 h. The reaction mixture was loaded onto silica gel (25 g) and washed with EtOAc (4×50 mL). The filtrate was concentrated in vacuo to a dark red oil. The oil was dissolved in EtOAc (100 mL) and washed with water (2×50 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (80 g silica gel, eluted with EtOAc in hexanes) to afford the desired product (1.28 g, 84%) as yellow oil. LCMS Anal. Calc'd for C17H20N2O4 316.1, found [M+H] 317.1. 1H NMR (500 MHz, CDCl3) δ 7.82 (d, J=8.0 Hz, 2H), 7.39 (s, 1H), 7.24-7.29 (m, 2H), 4.45 (d, J=18.2 Hz, 1H), 4.22-4.31 (m, 2H), 3.47 (d, J=18.2 Hz, 1H), 3.28-3.38 (m, 2H), 2.42 (s, 3H), 1.74 (s, 3H), 1.24 (t, J=7.0 Hz, 3H).

1. washwashed with EtOAc (4×50 mL)
2. concentrationThe filtrate was concentrated in vacuo to a dark red oil
3. dissolutionThe oil was dissolved in EtOAc (100 mL)
4. washwashed with water (2×50 mL)
5. dry with materialThe organic phase was dried over MgSO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel chromatography (80 g silica gel, eluted with EtOAc in hexanes)

ORD record

ord-2adb847b0d304088866ed523e01c2a8f

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791091B2