Sodium Chloride → Diethyl 2-methyl-3-oxopentanedioate

HRID 1793656Notes

Reaction equation

HRID 1793656 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:38])[CH:27]([CH3:37])[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:38])[CH:27]([CH3:37])[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 22022908HCID 22022908, compound

Product 1

HCID 10921903Diethyl 2-methyl-3-oxopentanedioate

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 753GlycerolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 40 mL of 300 mM potassium phosphate buffer, pH=6.5, containing NaCl (100 mM), DMSO (3% v:v), glucose (200 mM), and glycerol (10% v:v), 40 mM of 2-methyl-3-ketoketoglutarate diethyl ester was added along with 100 mg of lyophilized KRED 1008 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-0312240b097548b8b92e9321f813fe82
Source dataset
uspto-grants-2006_07
Patent number
US07081535B2

Reaction notes

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