Methyl iodide → (Rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

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Reaction Steps

1.37 g (3.04 mmol) of the above prepared (rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester and 0.95 ml (15.20 mmol) of methyl iodide were dissolved in 4.8 ml of N,N-dimethylformamide. After cooling (0° C.), 0.16 g (3.65 mmol) of NaH (55% in oil) was added. The reaction was stirred for 3 h at this temperature, then poured onto crushed ice/10% aq. potassium hydrogensulfate solution and extracted with diethyl ether (3×). The organic layers were washed with 10% aq. potassium hydrogensulfate solution and 10% aq. sodium chloride solution, dried over Na2SO4 and evaporated to dryness to yield 1.36 g (96%) of the title compound as light yellow oil. MS: 465.3 (MH+).

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