Triethylamine → N-(4-hydroxy-3-methoxybenzyl)-4-methyl-1,2-dithiolane-4-carboxamide

HRID 1915987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1915987
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1.C(N(CC)CC)C.[CH3:20][C:21]1([C:26](ON2C(=O)CCC2=O)=[O:27])[CH2:25][S:24][S:23][CH2:22]1>CC1OCCC1>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][NH:2][C:26]([C:21]2([CH3:20])[CH2:25][S:24][S:23][CH2:22]2)=[O:27])=[CH:5][C:6]=1[O:11][CH3:12]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 165576Phenol, 4-(aminomethyl)-2-methoxy-, hydrochloride (1:1)HCID 575054031-{[(4-Methyl-1,2-dithiolan-4-yl)carbonyl]oxy}pyrrolidine-2,5-dione

Produkt 1

HCID 45111293N-(4-hydroxy-3-methoxybenzyl)-4-methyl-1,2-dithiolane-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 73012-MethyltetrahydrofuranLösungsmittel

Versuchsvorschrift

24.3 mmol of N-hydroxysuccinimide are added to 24.3 mmol of dithiolane acid dissolved in 60 ml of dichloromethane cooled to 0° C. (on an ice bath). The reaction medium is stirred for 30 minutes at 0° C. A solution of 24.3 mmol of DCC in 50 ml of dichloromethane is added and the mixture is then stirred at 20° C. for 4 hours. The reaction medium is filtered and washed, and the filtrate is then evaporated to dryness on a rotavapor at 40° C. under vacuum to give 1-{[(4-methyl-1,2-dithiolan-4-yl)carbonyl]oxy}pyrrolidine-2,5-dione (m=7 g, quantitative yield). 10 ml of MeTHF, 3.16 mmol of 4-(aminomethyl)-2-methoxyphenol hydrochloride and 3.16 mmol of triethylamine are added to 1.58 mmol of 1-{[(4-methyl-1,2-dithiolan-4-yl)carbonyl]oxy}pyrrolidine-2,5-dione. After stirring overnight, the mixture is filtered, rinsed with MeTHF and then evaporated. Flash chromatography, eluting with 98/2 dichloromethane/methanol, gives Compound 16 in the form of a yellow oil (84% yield).

Aufarbeitung

  1. filtrationthe mixture is filtered
  2. washrinsed with MeTHF
  3. customevaporated
  4. washFlash chromatography, eluting with 98/2 dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-45a6fdd71c6f4f7b8e63beade604f60f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08617524B2

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