Reaction Steps
To a 0° C. solution of 2,2,5,5-tetramethyl-3-(2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86,89,92,95,98,101,104,107,110,113,116-nonatriacontaoxaoctadecahectan-118-yl)imidazolidin-4-one (1.42 g, 0.7 mmol) in methanol (150 ml) was added tert-butylhypochlorite (209 mg, 1.9 mmol). The mixture was stirred for 1 hour at 0° C. The reaction mixture was concentrated in vacuo, and crude material is purified by silica gel flash chromatography (0 to 10% methanol in dichloromethane) to give 775 mg (54%) of the title compound. 1H NMR (400 MHz, D2O) δ 3.72 (s, 152H), 3.65 (m, 2H), 3.58 (t, J=7.5 Hz, 2H), 3.40 (s, 3H), 1.55 (s, 6H), 1.38 (s, 6H). 13C NMR (100 MHz, D2O) δ 174.9, 83.6, 71.0, 69.5 (large peak) 67.7, 66.0, 58.1, 40.2, 24.2, 22.7.
