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), 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) 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-e289f9f443da4c6783c5426206f6b335
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07163814B2
Reaction notes
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