Hydrochloric Acid → N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine

HRID 465916

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=O.[C:13](Cl)(=[O:17])[O:14][CH2:15][CH3:16].[NH2:19][CH2:20][CH2:21][SH:22].Cl>C(Cl)Cl.C(N(CC)CC)C>[CH2:15]([O:14][C:13]([O:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([NH:19][CH2:20][CH2:21][SH:22])=[O:9])=[O:17])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: -15 °C

Versuchsvorschrift

Under argon atmosphere, 2.84 g of 4-methoxysalicylic acid was dispersed in 45 ml of methylene chloride, and the dispersion was cooled to -15° C. To the dispersion was added 3.76 g of triethylamine and 3.77 g of ethyl chlorocarbonate, and the mixture was agitated for 1.5 hour. To the mixture was added a solution of 1.56 g of cysteamine in 5 ml of methylene chloride, and the mixture was agitated at -15° C. for 2 hours. The reaction mixture was poured into 1N aqueous hydrochloric acid, and extracted with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off in evacuated atomosphere, and the residue was subjected to column chromatography using silica gel. There was obtained 4.50 g of N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine.

Aufarbeitung

stirringthe mixture was agitated at -15° C. for 2 hours
extractionextracted with methylene chloride
washThe organic layer was washed with saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off in evacuated atomosphere

Quellen und Nachweise

ORD-Eintrag: ord-3ae318039fa6472396b71c8f4c0654bb
Quelldatensatz: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05155106

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