Hydrochloric Acid → 4-(1-Hydroxy-2-(N-(2-hydroxyethyl)-2-nitrophenylsulfonamido)ethyl)phenyl 2-nitrobenzenesulfonate

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Reaction Steps

Sodium hydride (0.31 g, 7.0 mmol) was added to a solution of 3.0 g (5.82 mmol) of the title compound produced in step (i) of Reference Example 12 in N,N-dimethylformamide (19.1 ml), and the mixture was stirred at room temperature for 30 min. Thereafter, 1.65 g (5.82 mmol) of tert-butyl(2-iodoethoxy)dimethylsilane was added thereto, and the mixture was stirred at 100° C. for 21 hr. The reaction was stopped by adding sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure. Methanol (48 ml) was added to the concentrate, 11.6 ml (11.6 mmol) of 1 N hydrochloric acid was added thereto, and the mixture was stirred at room temperature for 30 min. Sodium hydrogencarbonate was added to stop the reaction, and methanol as the solvent was removed under the reduced pressure, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (chloroform:methanol=100:1) to give 2.22 g (yield 68%) of the title compound.

Provenance & Evidence