Sulfuric Acid → HCID 53328748, compound

HRID 1295529Notes

Reaction equation

HRID 1295529 reaction equation
O.[NH2:2][C@H:3]([C:9]([O-:11])=O)[CH2:4][CH2:5][C:6]([O-:8])=[O:7].[Na+].[Na+].[OH-].[Na+].[CH2:16]([CH:18]([CH2:22][CH2:23][CH2:24][CH3:25])[C:19](Cl)=[O:20])[CH3:17].S(=O)(=O)(O)O.[CH2:31]([NH2:35])[CH2:32][CH2:33][CH3:34]>O.CO.C1(C)C=CC=CC=1.CC(C)=O>[CH2:31]([N:35]([CH2:9][CH2:3][CH2:4][CH3:5])[C:9](=[O:11])[C@H:3]([CH2:4][CH2:5][C:6]([OH:8])=[O:7])[NH:2][C:19](=[O:20])[CH:18]([CH2:16][CH3:17])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:32][CH2:33][CH3:34]

Participants

10

Reactant 5

HCID 1118Sulfuric Acid3×HCID 8007Butylamine2×HCID 14798Sodium Hydroxide2×HCID 791032-Ethylhexanoyl chlorideHCID 18601051HCID 18601051, compound

Product 1

HCID 53328748HCID 53328748, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent3×HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

110 g of sodium glutamate monohydrate was dissolved in 140 g of water and 78 g of 27% aqueous sodium hydroxide and the solution was cooled to 10° C. The solution was added with 110 g of acetone and added dropwise with 87 g of 2-ethylhexanoyl chloride and 78 g of 27% aqueous sodium hydroxide. The reaction mixture for the acylation was diluted with 100 g of water and neutralized with 63 g of 95% sulfuric acid to separate an oil. The aqueous layer was removed, and the oil layer was concentrated under reduced pressure to obtain an oily substance. The resulting oily substance was dissolved in 742 g of methanol, and the solution was added with 6.2 g of 95% sulfuric acid and refluxed for 9 hours. The reaction mixture was left stand for cooling to 35° C. and neutralized with 8.8 g of n-butylamine, and then the methanol was evaporated to obtain an oily substance. The resulting oily substance was added with 643 g of toluene and 271 g of n-butylamine and the mixture was stirred with heating at 90° C. for 10 hours. The reaction mixture was added with 506 g of warm water and 130 g of 95% sulfuric acid to separate an oil, and the aqueous layer was removed. The oil layer was added with 1200 g of warm water, and the solvent was removed under ordinary pressure to obtain slurry of white solid. This solid was collected by filtration and dried in vacuo at 50° C. to obtain 2-ethylhexanoylglutamic acid dibutylamide.

Workup

  1. customto separate an oil
  2. customThe aqueous layer was removed
  3. concentrationthe oil layer was concentrated under reduced pressure
  4. customto obtain an oily substance
  5. temperaturerefluxed for 9 hours
  6. waitThe reaction mixture was left stand
  7. customthe methanol was evaporated
  8. customto obtain an oily substance
  9. customto separate an oil
  10. customthe aqueous layer was removed
  11. additionThe oil layer was added with 1200 g of warm water
  12. customthe solvent was removed under ordinary pressure
  13. customto obtain slurry of white solid
  14. filtrationThis solid was collected by filtration
  15. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-8230af68539345b0b80708b936321dc9
Source dataset
uspto-grants-2007_07
Patent number
US07244419B2

Reaction notes

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