Water → (Rac)-4-(3-hydroxy-1-methoxymethyl-propyl)-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

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Reaction Steps

3.22 ml (3.22 mmol, 1 M in tetrahydrofuran) tetrabutylammonium fluoride were added to a cooled solution (0° C.) of 1.36 g (2.93 mmol) (rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester in 29 ml tetrahydrofuran. After 50 min water was added and extracted with ethyl acetate (3×). The organic phases were washed with water (2×), dried over Na2SO4 and evaporated. Flash chromatography on silica gel with a gradient 2% to 4% methanol in dichloromethane yielded 0.79 g (77%) of the title compound as a colorless oil, MS: 263 (M).

Provenance & Evidence