1,2-Dibromoethane → HCID 69588086, compound

Participants

Reaction Conditions

Reaction Steps

1,2-Dibromoethane (11 mL, 125 mmol) and K2CO3 (15.5 g, 112.3 mmol) are added to a 2-[3-methoxy-2-(2-nitro-benzenesulfonylamino)-propionylamino]-3-naphthalen-2-yl-propionic acid methyl ester, 59, (6.4 g, 12.4 mmol) solution in anhydrous DMF (30 mL). The reaction mixture is stirred at 60° C. overnight. The reaction mixture is cooled to room temperature and the pH is adjusted to 3 with 1M KHSO4. The solution is extracted with EtOAc (3×100 mL) and the organic layers are combined and dried over Na2SO4. The solvent is removed in vacuo to afford 5.6 g (85% yield) of the desired product. 1H NMR (300 MHz, CDCl3, δ): 7.89 (m, 1H), 7.70 (m, 3H), 7.57 (m, 3H), 7.47 (m, 1H), 7.41 (m, 2H), 7.30 (d, J=8.6 Hz, 1H), 5.39 (m, 1H), 4.37 (s, 3H), 3.62 (m, 4H), 3.46 (m, 2H), 3.35 (m, 1H), 3.20 (m, 2H), 3.13 (s, 3H); 13C NMR, δ 170.4, 165.7, 156.5, 147.9, 134.2, 134.1, 133.6, 133.4, 132.6, 132.4, 130.8, 128.4, 127.8, 127.7, 127.2, 126.4, 126.0, 124.6, 74.1, 65.0, 58.9, 58.1, 52.7, 44.3, 41.8, 34.3.

Provenance & Evidence