1,2-Dichloroethane → HCID 58813160, compound

Participants

Reaction Steps

Step B (1): DIEA (1.35 mL, 9.9 mmol) was added to a mixture of (S)-2-allylhexanoic acid (300 mg, 1.92 mmol), methyl 2-aminoacetate hydrochloride (254 mg, 2.02 mmol), EDC (387 mg, 2.02 mmol), HOBt (273 mg, 2.02 mmol) in DMF (15 mL) at room temperature. The mixture was stirred for 18 h. Poured the reaction mixture into 200 mL 1 M HCl. Extracted with EtOAc/Hex (95:5) (2×200 mL). Washed combined organic extracts with brine, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (5-50% EtOAc/hexanes linear gradient) to give (S)-methyl 2-(2-allylhexanamido)acetate 360 mg (83% yield) as white solid: ESI (M+H)+=228.2; 1H NMR (500 MHz, CDCl3) δ 5.90 (s, 1H), 5.64-5.85 (m, 1H), 4.95-5.14 (m, 2H), 4.04 (dd, J=5.04, 2.29 Hz, 2H), 3.75 (s, 3H), 2.28-2.46 (m, 1H), 2.07-2.29 (m, 2H), 1.62-1.64 (m, 1H), 1.46-1.47 (m, 1H), 1.18-1.36 (m, 4H), 0.87 (t, J=6.87 Hz, 3H).

Provenance & Evidence