Benzyl Bromide → HCID 9847467, compound

Participants

Reaction Conditions

Reaction Steps

The title C compound, 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide (0.58 mmol, 220 mg) is dissolved in 15 mL of THF and cooled to −78° C. LHMDS (1.2 mmol, 1.2 mL of 1.0 M solution) is added and the mixture is stirred to 1 h at −78° C. Benzyl bromide (0.6 mmol, 103 mg) is added and the mixture stirred at −78° C. for 2 h further. The reaction mixture is quenched with aqueous saturated ammonium chloride, the solvent is evaporated and the residue is partitioned between EtOAc and brine. The organic solution is dried and evaporated to an oil. Chromatography on silica (eluent: 35% EtOAc in hexanes) affords 3-cyclopentyl-2-[4-(2-phenyl-ethanesulfonyl)-phenyl]-N-thiazol-2-yl-propionamide: 1H NMR δ 11.8 (s, 1H), 7.86 (d, J=8, 2H), 7.55 (m, 3H), 7.05-7.32 (m, 6H) 3.8 (t, J=7.5, 1H), 3.33 (m, 2H), 3.05 (m, 2H), 2.29 (m, 1H), 1.0-1.9 (m, 8H); e/z (ES) 469 (M+1, 100%).

Provenance & Evidence