Methyl iodide → HCID 69686346, compound

Participants

Reaction Steps

A mixture of 2-[6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,7-dioxo-[1,2]diazepan-1-yl]-propionic acid tert-butyl ester (14) (314 mg, 0.84 mmol), benzyltriethylammonium chloride (30 mg, 0.13 mmol), K2CO3 (406 mg, 2.94 mmol) and iodomethane (360 mg, 2.53 mmol) in THF (8 mL) was stirred at room temperature for five days. The mixture was diluted with dichloromethane (70 mL), washed with water three times, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to dryness to afford 296 mg (91% yield) of the title compound as a mixture of diastereomers. 1H-NMR (500 MHZ, CDCl3) δ 1.25-1.35 (m, 2.5H), 1.47-1.52 (m, 0.5H), 1.60-1.75 (m, 3H), 2.37-2.52 (m, 2H), 3.05-3.14 (m, 0.5H), 3.30-3.45 (m, 3.5H), 3.45-3.58 (m, 1H), 4.14-4.28 (m, 2H), 4.52-4.58 (m, 0.5H), 4.80-4.87 (m, 0.5H), 5.13-5.28 (m, 1H), 7.70-7.90 (m, 4H). Analytical HPLC: 6.00 and 6.11 min. LC-MS (ES+): m/e=388 (M+H+).

Provenance & Evidence