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N-(2-formyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamide → 7-N-acetyldemethyllavendamycin methyl ester

HRID 1760193
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1760193
[C:1]([NH:4][C:5]1[C:14](=[O:15])[C:13]2[N:12]=[C:11]([CH:16]=O)[CH:10]=[CH:9][C:8]=2[C:7](=[O:18])[CH:6]=1)(=[O:3])[CH3:2].CN(C[CH2:23][O:24][C:25](=[O:39])[C@H:26]([CH:28](C)[C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)[NH2:27])C>C1(OC)C=CC=CC=1>[CH3:2][C:1]([NH:4][C:5]1[C:14](=[O:15])[C:13]2[N:12]=[C:11]([C:16]3[N:27]=[C:26]([C:25]([O:24][CH3:23])=[O:39])[CH:28]=[C:29]4[C:37]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[NH:31][C:30]=34)[CH:10]=[CH:9][C:8]=2[C:7](=[O:18])[CH:6]=1)=[O:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 11586798N-(2-formyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamideHCID 54068225b-Methyltryptophan n,n-dimethylaminoethyl ester

Produkt 1

HCID 116621517-N-acetyldemethyllavendamycin methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7519AnisoleLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7-N-Acetyllavendamycin N-N-Dimethylaminoethyl Ester (Compound 19. Table l): 7-Acetamido-2-formylquinoline-5,8-dione (23) (prepared as described in Example 23) (317 mg, 0.13 mmol) was dissolved in 16 ml of dry anisole and heated to 80° C. b-methyltryptophan N,N-dimethylaminoethyl ester (41) (prepared as described in Example 41) (37.5 mg, 0.13 mmol) was added with stirring, and the stirred mixture was heated at 100° C. for 5.5 hr. The reaction mixture was allowed to cool to room temperature and the solid was filtered. The filtrate was distilled under vacuum to dryness. Ethyl acetate (3 ml) was added, and the mixture was stirred. Upon filtration 24.5 mg (a yield of 36%) of an orange solid was obtained.

Aufarbeitung

  1. additionwas added
  2. temperatureto cool to room temperature
  3. filtrationthe solid was filtered
  4. distillationThe filtrate was distilled under vacuum to dryness
  5. additionEthyl acetate (3 ml) was added
  6. stirringthe mixture was stirred
  7. filtrationUpon filtration 24.5 mg (a yield of 36%) of an orange solid
  8. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-fd08f8df3ddb446384a134850f338916
Quelldatensatz
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06841555B2

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