Diisopropylethylamine → HCID 68567290, compound

Participants

Reaction Steps

To a solution of the intermediate from step G (39.7 mg, 0.08 mmol) in 3 mL of anhydrous DMF was added ethyl β-alaninate hydrochloride (19 mg, 0.12), 1-hydroxy-7-azabenzo-triazole (17 mg, 0.12 mmol), N,N-diisopropylethyl amine (0.04 mL, 0.24 mmol), and 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (24 mg, 0.12 mmol). The reaction was left stirring at room temperature for 12 hours then diluted with EtOAc and washed with 1N HCl (2×), saturated sodium bicarbonate (2×), and brine (1×). The organic layer was then dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting solid was purified by flash chromatography (30% EtOAc/Hexanes) to afford a light yellow solid. Enantiomers were then separated using SFC-HPLC semi-prep methodology with the conditions as follows: column=ChiralCel OJ 10×250 mm 10 micron, flow rate=10.0 mL/min, mobile Phase=40% MeOH (0.1% TFA)/CO2, column temperature=40° C., UV wavelength=248 nm, outlet pressure=100 bar, concentration=50 mg/mL in MeOH. Retention time: Isomer A=4.03 min; Isomer B=5.01 min. LC-MS: 4.20 min. (M+H)=589.48.

Provenance & Evidence