Sodium Chloride → 2-Isobutyl-3-ketoglutarate diethyl ester

HRID 1793657Notes

Reaction equation

HRID 1793657 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Na+].[Cl-].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH2:23]([O:25][C:26](=[O:41])[CH:27]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:28](=[O:36])[C:29](=O)[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:24]>C(OCC)(=O)C.OCC(CO)O.CS(C)=O>[CH2:23]([O:25][C:26](=[O:41])[CH:27]([CH2:37][CH:38]([CH3:39])[CH3:40])[C:28](=[O:36])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:24]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 220229102-Isobutyl-3-ketoketoglutarate diethyl ester

Product 1

HCID 99926592-Isobutyl-3-ketoglutarate diethyl ester

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 753GlycerolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 40 mL of 300 mM potassium phosphate buffer buffer, pH=6.5, containing NaCl (100 mM), DMSO (3% v:v), glucose (200 mM), and glycerol (10% v:v), 40 mM of 2-isobutyl-3-ketoketoglutarate diethyl ester was added along with 100 mg of lyophilized KRED 1001 and 30 mg of glucose dehydrogenase. The reaction mixture was incubated for 48 hours at 37 C. Gas chromatographic analysis showed that the yield of hydroxy diester product was greater than 80%. The product was isolated by extraction of the reaction mixture with ethyl acetate and purification using silica gel chromatography. Isolated yield was in the range of 85–95%.

Workup

  1. customIsolated
  2. customyield

Sources & evidence

ORD record
ord-cb2716e4893e47f5b420d1a47f407af7
Source dataset
uspto-grants-2006_07
Patent number
US07081535B2

Reaction notes

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