1-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]-2-methoxyethane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of benzyl 4-mercapto-2-methylbutan-2-ylcarbamate (20 mmol) in N,N-dimethylformamide (20 ml) was added cesium carbonate (6.49 g, 19.9 mmol) and 13-bromo-2,5,8,11-tetraoxatridecane (5.00 g, 18.4 mmol). The solution was stirred for 16 hours, concentrated in vacuo, and the residue dissolved in 500 ml ethylacetate, washed with 3 times with 100 ml 5% NaHSO4, 1×200 ml sat. NaCl, dried on MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography (10% to 60% ethylacetate in hexanes) to give the titled compound as a clear oil (7.47 g, 18.1 mmol, 98%). 1H NMR (400 MHz, CDCl3) δ 1.31 (s, 6H), 1.95-1.99 (m, 2H), 2.51-2.55 (m, 2H), 2.69-2.73 (m, 2H), 3.38 (s, 3H), 3.54-3.58 (m, 2H, 3.6-3.7 (m, 14H), 4.77 (br s, 1H), 5.06 (s, 2H), 7.3-7.4 (m, 5H). LRMS (ESI/APCI): 466 [M+Na]+. concentrated in vacuo the residue dissolved in 500 ml ethylacetate washed with 3 times with 100 ml 5% NaHSO4, 1×200 ml sat. NaCl dried on MgSO4 concentrated in vacuo The residue was purified by flash chromatography (10% to 60% ethylacetate in hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2.0 g (3.83 mmol) of N-[3-hydroxy-5-(octadecyloxy)phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester, 4.15 g (15.3 mmol) of 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl bromide, 1.2 g (7.66 mmol) ofsodium iodide and 1.6 g (11.5 mmol) of potassium carbonate in 60 ml of acetone and 30 ml of DMF was stirred at reflux for 48 hours. The solvents were removed at reduced pressure and the residual oil was purified by HPLCusing 60% ethyl acetate-hexane to give 2.01 g (73% yield) of N-[3-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]-5-(octadecyloxy)phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester. The nmr and mass spectra were consistent with the structure. at reflux for 48 hours The solvents were removed at reduced pressure the residual oil was purified