Sulfuric Acid → HCID 86586297, compound

HRID 1295530Notes

Reaction equation

HRID 1295530 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+].[C:16](Cl)(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].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:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:32][CH2:33][CH3:34]

Participants

10

Reactant 5

HCID 1118Sulfuric Acid3×HCID 8007Butylamine2×HCID 8124Octanoyl chlorideHCID 14798Sodium Hydroxide2×HCID 18601051HCID 18601051, compound

Product 1

HCID 86586297HCID 86586297, 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 cooled to 10° C. The solution was added with 110 g of acetone and added dropwise with 87 g of octanoyl chloride and 90 g of 27% aqueous sodium hydroxide. The reaction mixture for the acylation was diluted with 100 g of water and neutralized with 64 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 10.5 g of n-butylamine, and then the methanol was evaporated to obtain an oily substance. The resulting oily substance was added with 630 g of toluene and 191 g of n-butylamine and the mixture was stirred with heating at 90° C. for 10 hours. The reaction mixture was added with 500 g of warm water and 178 g of 95% sulfuric acid to separate an oil, and the aqueous layer was removed. The oil layer was added with 645 g of warm water, and the solvent was removed under ordinary pressure to obtain slurry of white solid. The resulting solid was collected by filtration and dried in vacuo at 50° C. to obtain octanoylglutamic 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 645 g of warm water
  12. customthe solvent was removed under ordinary pressure
  13. customto obtain slurry of white solid
  14. filtrationThe resulting solid was collected by filtration
  15. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-6da8acb67a684f109e9590f74fc1dcb6
Source dataset
uspto-grants-2007_07
Patent number
US07244419B2

Reaction notes

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