Sodium Carbonate → methyl (S)-4-bromo-3-hydroxybutyrate

Participants

Reaction Steps

A solution was prepared by dissolving 75 g of glucose, 0.85 g of oxidized form of nicotine adenine dinucleotide phosphate, 0.11 g of glucose dehydrogenase (glucose amino 2; by Amano enzyme) in 1500 g of a phosphate buffer solution (pH 6.5) and 1300 g of butyl acetate and 37 g of methyl 4-bromo-3-oxobutanoate were added thereto, and then 150 g of the acetone-treated cells of Penicillium citrinum IFO 463described above were added to thereto under stirring. 15% aqueous sodium carbonate solution was dropwise added thereto so that the pH of the reaction solution is maintained within a range of from 6.5±0.5. After stirring for 24 hours, 90 g of celite were added thereto and filtered under reduced pressure. The organic layer separated from the filtrate was concentrated under reduced pressure to give 28 g of methyl (S)-4-bromo-3-hydroxybutanoate, Chemical Purity: 88%, Optical purity: 97% e.e.

Provenance & Evidence