Sodium hydride → Isohexane ethyl acetate

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Reaction Steps

Sodium hydride (0.026 g of a 60% dispersion in oil) was added to a mixture of 2,3-dichloro-N-(3,5-dibromo-2-pyrazinyl)benzenesulphonamide (Example 31a) (0.1 g) and 2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (0.088 g) in 1,2-dimethoxyethane (2 mL). After 0.5 h, the reaction mixture was partitioned between 2N hydrochloric acid and ethyl acetate. The organic solution was dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the title compound protected with the BOC (tert-butoxycarbonyl) group (0.11 g) as an oil. This product was dissolved in dichloromethane (6 mL) and trifluoroacetic acid (2 mL). After 2 h, toluene was added and the solution evaporated to dryness. Crystallisation from diethyl ether gave the product as a white solid (0.083 g).

Provenance & Evidence