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

HRID 2112378Notes

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>[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 and 30 ml of 100 mM phosphate buffering solution (pH 7.0) were mixed and stirred at 30° C. for 27 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 2.4 g of ethyl 2-hydroxy-4-phenylbutyrate. The optical purity of the resulting ethyl 2-hydroxy-4-phenylbutyrate was measured, to find 98.5% 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-d3a480e490b841018fefbacad83d3226
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524666B2

Reaction notes

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