Ethyl Acetate → HCID 58420493, compound

Participants

Reaction Conditions

Reaction Steps

A mixture containing compound (12) (3.0 g, 6.86 mmol), compound (10) (1.32 g, 10.3 mmol), anhydrous DIEA (6.03 ml, 34.3 mmol, dried over 4 Å sieves), and anhydrous N,N-dimethyl acetamide (DMA) (40 mL) is heated at 80° C. under an atmosphere of argon gas. After heating for 1 h, the reaction mixture is cooled to room temperature, diluted with EtOAc (200 mL), and washed with water (100 mL). The aqueous layer is extracted with EtOAc (100 mL), and the combined organic layers are washed with a saturated aqueous solution of sodium bicarbonate (100 mL). The organic layer is diluted with water (100 mL) and treated with an aqueous solution of HCl (4 N) until the aqueous layer is acidic (pH 2-3 after shaking the mixture vigorously). The organic layer is separated, and this process is repeated. The combined aqueous layers are diluted with EtOAc (100 mL) and treated with an aqueous solution of sodium hydroxide (6 N) until the aqueous layer is basic (pH ˜8 after shaking the mixture vigorously). The aqueous layer is separated, and this process is repeated. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure giving an orange solid (4.8 g). 1H-NMR (CDCl3): δ 0.36-0.41 (1H, m), 0.83-0.88 (1H, m), 0.98-1.03 (1H, m), 1.19 (6H, d, J=1.8 Hz), 1.18-1.26 (1H, m), 1.38 (3H, t, J=6.0 Hz), 1.71-1.78 (1H, m), 1.98-2.03 (1H, m), 2.22-2.34 (1H, m), 3.36-3.50 (2H, m), 3.43 (3H, s), 3.82-3.91 (1H, m), 4.02-4.13 (2H, m), 4.36-4.47 (2H, m), 6.19 (1H, t, J=75 Hz), 7.62 (1H, d, J=13.8 Hz); 19F: δ −121.3, −82.9 (d, J=39.5 Hz); LRMS calc. for C24H30F3N3O6S 545, found 546 (M+1).

Provenance & Evidence