Benzyl bromoacetate → Diethylether hexane

Participants

Reaction Steps

Sodium salt H-1a (1.13 g; 3.15 mmol) was suspended in 5 mL dry toluene and tetra-n-butyl ammonium bromide (0.10 g; 0.3 mmol) and benzyl bromoacetate (0.79 g; 3.45 mmol) were added and the solution was refluxed for 24 h. The solvent was removed and methylene chloride added to the residue. The solution was filtered through silica gel, the filtrate was evaporated and the crude product E-1k purified by flash chromatography using silica gel and a hexane/ether gradient (0.39 g; 26% yield). 1H NMR (CDCl3): δ0.95 (dd,6H), 1.45 (s,9H), 1.78 (m,2H), 1.92 (m,1H), 3.28-3.55 (m,4H), 4.08 (t,1H), 4.32 (s,2H), 5.07 (br t, 1H), 5.21 (s,2H), 7.34 (m,5H). 13C NMR: δ22.36, 24.34, 28.26, 39.03, 39.64, 40.42, 47.87, 64.77, 67.89, 79.71, 128.28, 128.37, 128.57, 134.59, 155.78, 165.38, 166.84. This derivative of E-1, E-1k, can be readily deblocked and elaborated further to yield additional inhibitors.

Provenance & Evidence