Water → Benzyl (2S,3S)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionate

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Reaction Steps

(2S,3S)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionic acid (1.40 g) obtained in Example 9 and sodium bicarbonate (712 mg) were suspended in dimethylformamide (20 ml). A dimethylformamide (20 ml) solution of benzyl bromide (3.56 g) was added to the resultant suspension, and the suspension was stirred at room temperature for 24 hours. Water was added after the reaction, and then was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated sodium chloride solution. After the resultant layer was dried with magnesium sulfate, the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (a developing solvent; hexane:ethyl acetate=1:1→1:3) to obtain 1.13 g of a target compound. NMR data of the compound were as follows.

Provenance & Evidence