alpha Lipoic acid → Lipoic acid

Participants

Reaction Steps

Diisopropylethylamine (DIPEA) (anhydrous, 4.3 ml, 24.2 mmol) was added to a solution of EDC.HCl (604 mg, 3.15 mmol) in dichloromethane (15 ml) and stirred for 10 minutes. N-hydroxysuccinimide (390 mg, 3.39 mmol) was added followed by DL-lipoic acid (500 mg, 2.43 mmol). The reaction mixture was stirred in an ice bath for half an hour and then slowly continued overnight under room temperature. The reaction mixture was washed with HCl (5% v/v, 25 ml×2) and water (50 ml×3). The organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified by silica gel column chromatography (ethylacetate/hexane=2:1) (618 mg, 85%); 1H-NMR (CDCl3) 1.62-1.98 (7H, m), 2.29-2.47 (1H, m), 2.69 (2H, t, J=7.4), 3.02 (4H, s, succinimidyl CH2×2), 3.21-3.28 (2H, m), 3.60-3.65 (1H, m); ESI-MS m/z calcd for C12H17NO4S2: 303.2518. found: 304.1861 [M+1].

Provenance & Evidence