Phosphate → Methyl 4-bromo-3-oxobutanoate
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][CH:3]([OH:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:1][CH2:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6]Participants
Reactant 5
Product 2
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), 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.
Workup
- custom(1000×g, 5 min)
- customto collect the organic layer
Sources & evidence
- ORD record
- ord-f0123700b11e418aa0b3b3be361410d8
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07163814B2
Reaction notes
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