Hydrochloric Acid → (R)-1-Methyl hydrogen 3-methylglutarate

HRID 35717Notes

Reaction equation

HRID 35717 reaction equation
OP([O-])(O)=O.[K+].[CH3:7][CH:8]([CH2:14][C:15]([O:17]C)=[O:16])[CH2:9][C:10]([O:12][CH3:13])=[O:11].C(=O)([O-])[O-].[K+].[K+].Cl>CO>[CH3:13][O:12][C:10](=[O:11])[CH2:9][C@H:8]([CH3:7])[CH2:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 516951Monobasic potassium phosphateHCID 519624Dimethyl 3-methylglutarate

Product 1

HCID 6999733(R)-1-Methyl hydrogen 3-methylglutarate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 5 1. four necked flask fitted with a stirred and pH electrode was added 2.5 1. of 0.1M potassium acid phosphate buffer pH 7.0 followed by 150 mg. of pig liver esterase and 150 g. of dimethyl 3-methylglutarate. The pH of the mixture was maintained at about 6.85 by periodic addition of a 10% potassium carbonate solution. After 2.5 hours the reaction was acidified with 10% hydrochloric acid to pH 2.0 and the product extracted with diethyl ether. The extracts were combined, dried over magnesium sulfate and concentrated in vacuo to give 114 g. of the desired product, [alpha]D =-1.48 (CH3OH C=0.086 g/ml).

Workup

  1. customfour necked flask fitted with
  2. additionwas added 2.5 1
  3. extractionthe product extracted with diethyl ether
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give 114 g

Sources & evidence

ORD record
ord-cf9fac91e8dc48da9b6482790afa4af9
Source dataset
uspto-grants-1988_08
Patent number
US04767743

Reaction notes

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