Sodium hydride → HCID 86620260, compound

Participants

Reaction Steps

NaH (107 mg, 2.69 mmol, 60% in oil) was added to a solution of 212 (1.3 g, 2.24 mmol) in DMF (15 mL) at 0° C. 1,3-Dichloropropene (414 mg, 3.36 mmol, mixed isomers) was added and the mixture was allowed to warm to room temperature over 12 h. The DMF was evaporated under reduced pressure and the residue was partitioned between EtOAc and H2O. The EtOAc layer was washed with H2O, brine, then dried and evaporated. The residue was purified by chromatography on silica gel, eluting with petroleum ether/EtOAc (4:1) to give tert-butyl 1-bromo-7-[(dibenzylamino)sulfonyl]-2-naphthyl(3-chloro-2-propen-1-yl)carbamate (213) (1.39 g, 95%) as a yellow foam: 1H NMR (CDCl3) (mixture of rotamers and E and Z forms) δ 8.86 (s, 1H), 7.97-7.91 (m, 1H), 7.89-7.82 (m, 2H), 7.51-7.31, 7.26-7.16 (2 m, 7H), 7.13-7.06 (m, 4H), 6.14-6.01 (m, 2H), 4.64-4.48, 4.02-3.90 (2 m, 2H), 4.43 (s, 4H), 1.56, 1.33 (2 s, 9H). HRMS (FAB) calcd. for C32H3279Br35ClN2O4S (M) 655.1033, found 655.1032.

Provenance & Evidence