Phosphate → Methyl 4-bromo-3-oxobutanoate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-bromo-3-oxobutyrate (300 mg), the above-mentioned wet bacterial cells (0.4 g), NADP+ (9 mg), glucose (750 mg), 100 mM phosphate buffer (pH 6.5) (15 ml) and butyl acetate (15 ml) were mixed. The mixture was stirred at 30° C. for 7 hr. During the stirring, 2M aqueous sodium carbonate solution was gradually added to adjust the pH of the reaction solution to 6.5±0.2. After the stirring had been finished, the reaction solution was centrifuged (1000×g, 5 min) to collect the organic layer. The organic layer was subjected to an analysis for content using gas chromatography under the following condition. Methyl 4-bromo-3-hydroxybutyrate was produced 98.5% to the amount of the methyl 4-bromo-3-oxobutyrate used in the reaction. Furthermore, the optical purity of methyl 4-bromo-3-hydroxybutyrate in the organic layer was measured at the following condition, which resulted in 99% e.e. of (S)-form. The organic layer was concentrated to give crude methyl (S)-4-bromo-3-hydroxybutyrate.

Provenance & Evidence