Triethylamine → HCID 59294388, compound

Participants

Reaction Steps

To a solution of (R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochloride (1 g, 3.2 mmol), triethylamine (1.3 mL, 9.6 mmol) and DMAP (20 mg, 0.16 mmol) in anhydrous CH2Cl2 (25 mL) was added 5-bromothiophene-2-sulfonyl chloride (2.5 g, 9.6 mmol). Methylene chloride (200 mL) was added and the solution was washed with dilute NaOH (10 mL), water (10 mL), dried over MgSO4 and concentrated to dryness. The residue was purified by silica gel chromatography (95:5 CH2Cl2/MeOH) to give the title compound as a yellow solid (650 mg, 44%). 1H NMR (400 MHz, CDCl3) δ 7.44 (d, 1H, J=3.8 Hz), 7.41-7.27 (m, 5H), 7.04 (d, 1H, J=3.8 Hz), 5.14-5.07 (m, 2H), 3.87-8.83 (m, 1H), 2.92-2.89 (m, 1H), 2.83-2.78 (m, 1H), 2.69-2.64 (m, 1H), 2.60-2.54 (m, 1H), 2.43 (s, 6H); MS ESI 461.3 [M+H]+, calcd for [C17H21BrN2O4S2]+ 461.00.

Provenance & Evidence