Acetone → HCID 22940784, compound

HRID 1459149Notes

Reaction equation

HRID 1459149 reaction equation
[NH2:1][C@H:2]([C:17]([OH:19])=[O:18])[CH2:3][CH2:4][C:5]([NH:7][C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:6].CC(C)=O.[C:24](Cl)(=[O:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].Cl>O.[OH-].[Na+]>[C:24]([NH:1][C@H:2]([C:17]([OH:19])=[O:18])[CH2:3][CH2:4][C:5]([NH:7][C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:6])(=[O:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8166Dodecanoyl chloride3×HCID 92865N-(4-Amino-4-carboxy-1-hydroxybutylidene)glutamic acid

Product 1

HCID 22940784HCID 22940784, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
10 °C

Procedure

A suspension of 16 g (0.058 mols) of γ-glutamylglutamic acid in 55 ml of water was dissolved in a 27-% sodium hydroxide aqueous solution until the pH reached 11, and 27 ml of acetone were added thereto. To the solution were added dropwise 12.6 g (0.058 mole) of lauroyl chloride over a period of 1 hour. When adding lauroyl chloride, the temperature was maintained at 10° C., and 27-% sodium hydroxide was added dropwise simultaneously to keep the pH at 11. After the completion of the addition of lauroyl chloride, the reaction solution was warmed at 30° C., and allowed to stand for 30 minutes. Subsequently, the pH was adjusted to 1 with the addition of conc. hydrochloric acid. The solid precipitate was separated by filtration, and dried to obtain 23.6 g of N-(N'-lauroyl-γ-glutamyl)glutamic acid in a yield of 89%. This solid was analyzed by infrared spectrophotometry. A peak diagnostic of an amide group was observed at 1,640 cm-1 and a peak diagnostic of a carboxyl group was observed at 1,730 cm-1, respectively. FAB mass spectrum: 459 (MH+).

Workup

  1. additionwere added
  2. temperaturethe reaction solution was warmed at 30° C.
  3. customThe solid precipitate was separated by filtration
  4. customdried

Sources & evidence

ORD record
ord-287a3bfe757b47a6a7b81b65e16c067c
Source dataset
uspto-grants-1998_12
Patent number
US05854199

Reaction notes

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