Phosphate → Ethyl 2-hydroxy-4-phenylbutyrate, (+-)-

HRID 2112379Notes

Reaction equation

[O:1]=[C:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].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+].S([O-])([O-])(=O)=O.[Mg+2]>C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.C(OCC)(=O)C.C(OCCCC)(=O)C>[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

Conditions

Temperature: 30 °C

Procedure

3.0 g of ethyl 2-oxo-4-phenylbutyrate, 0.49 g of the above-mentioned wet cell, 3.0 mg of NAD+, 4.5 g of glucose, 30 ml of 100 mM phosphate buffering solution (pH 7.0) and 6 ml of butyl acetate were mixed and stirred at 30° C. for 9 hours. During stirring, 2M sodium carbonate aqueous solution was added gradually so that the reaction solution had a pH of 7.0. Thereafter, to the reaction liquid was added 50 ml of ethyl acetate, then, centrifugal separation was performed to obtain an organic layer. This organic layer was dehydrated over magnesium sulfate, and ethyl acetate was distilled off, to obtain 3.0 g of ethyl 2-hydroxy-4-phenylbutyrate. The optical purity of the resulting ethyl 2-hydroxy-4-phenylbutyrate was measured, to find 100% e.e. for (R) configuration.

Workup

stirringDuring stirring
customThereafter, to the reaction liquid
customcentrifugal separation
customto obtain an organic layer
distillationwas distilled off

Sources & evidence

ORD record: ord-34aaaf1a07634eae99328441b588f06e
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524666B2

Reaction notes

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