Acetone → HCID 22940783, compound

HRID 1459147Notes

Reaction equation

[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH: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:8]([NH:10][C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[OH:7])(=[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

Conditions

Temperature: 10 °C

Procedure

A suspension of 20 g (0.0724 mols) of α-glutamylglutamic acid in 70 ml of water was dissolved in a 27-% sodium hydroxide aqueous solution until the pH reached 11, and 35 ml of acetone were added thereto. To the solution were added dropwise 15.8 g (0.0724 mols) 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 constant. After 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 30.6 g of N-(N'-lauroyl-α-glutamyl)glutamic acid in a yield of 92%. This solid was analyzed by infrared spectrophotometry. A peak diagnostic of an amide group was observed at 1,650 cm-1 and a peak diagnostic of a carboxyl group was observed at 1,730 cm-1, respectively.

Workup

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

Sources & evidence

ORD record: ord-e98289a636204636ace0d187bb8c5477
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854199

Reaction notes

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