Triethylamine → HCID 86758388, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-[1,2]diazepan-1-yl]-acetic acid tert-butyl ester (21) (155 mg, 0.42 mmol), triethylamine (0.5 mL) and 4-N,N-dimethylaminopyridine (DMAP) (101 mg, 0.50 mmol) in dichloromethane was added dropwise methanesulfonyl chloride (95 mg, 0.83 mmol). The mixture was stirred at 0° C. for 5 min then at room temperature for 16 hours. The mixture was quenched with water, extracted with dichloromethane. The organic solution was washed with water then brine, dried over anhydrous Na2SO4, filtered and purified by flash chromatography using dichloromethane/ethyl acetate (99/1 to 95/5) to afford 154 mg (82% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.47 (s, 9H), 2.05-2.21 (m, 2H), 2.83-2.87 (m, 1H), 3.27 (s, 3H), 3.53-3.58 (m, 1H), 4.07-4.11 (d, 1H), 4.29-4.33 (m, 1H), 4.50-4.53 (d, 1H), 5.42-5.44 (m, 1H), 7.70-7.85 (m, 4H). Analytical HPLC: 12.27 min. LC-MS (ES+): m/e=452 (M+H+).

Provenance & Evidence