Phosphate → methyl (S)-4-bromo-3-hydroxybutyrate
Reaction equation
[Br:1][CH2:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.P([O-])([O-])([O-])=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCCCC)(=O)C>[Br:1][CH2:2][C@@H:3]([OH:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
Methyl 4-bromo-3-oxobutyrate (300 mg), the above-mentioned wet bacterial cells (0.4 g), NADP+ (9 mg), glucose (750 mg), glucose dehydrogenase (manufactured by Amano Pharmaceuticals, Co., Ltd.) (1.2 mg), 100 mM phosphate buffer (pH 6.5) (15 ml) and butyl acetate (15 ml) are mixed. The mixture is stirred at 30° C. for 7 hr. During the stirring, 2M aqueous sodium carbonate solution is gradually added to adjust the pH of the reaction solution to 6.5±0.2. After the stirring has been finished, the reaction solution is centrifuged (1000×g, 5 min) to collect the organic layer. The organic layer is subjected to an analysis for content using gas chromatography under the following condition. The optical purity of methyl 4-bromo-3-hydroxybutyrate in the above-mentioned organic layer was also determined under the following condition. The organic layer was concentrated to give crude methyl (S)-4-bromo-3-hydroxybutyrate.
Workup
- custom(1000×g, 5 min)
- customto collect the organic layer
- concentrationThe organic layer was concentrated
Sources & evidence
- ORD record
- ord-ff304b25119448c08723d01c7943791e
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07135318B2
Reaction notes
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