Phenyl glycidyl ether → YM 16151-1

HRID 4663

Reaktionsgleichung

Reaktionsgleichung von HRID 4663
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[CH:16]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:26])[NH:19][C:18]([CH3:27])=[C:17]1[C:28]([O:30][CH3:31])=[O:29].[C:32]1([O:38][CH2:39][CH:40]2[O:42][CH2:41]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CO>[OH:42][CH:40]([CH2:39][O:38][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:41][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[CH:16]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:26])[NH:19][C:18]([CH3:27])=[C:17]1[C:28]([O:30][CH3:31])=[O:29]

Komponenten

4

Edukt 2

HCID 31217Phenyl glycidyl etherHCID 14306630Dimethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Produkt 1

HCID 128387YM 16151-1Ausbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In 1,300 ml of methanol were dissolved 13 g of dimethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 4.5 g of glycidyl phenyl ether, and the solution thus formed was refluxed under heating for 16 hours. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chloroform-methanol (96:4 v/v). Crude crystals were recrystallized from ethanol to give 9 g of dimethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate.

Aufarbeitung

  1. customthe solution thus formed
  2. temperaturewas refluxed
  3. temperatureunder heating for 16 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. washthe product was eluted with chloroform-methanol (96:4 v/v)
  6. customCrude crystals were recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3c162ac0662642e38fab20fffb0079d3
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727082

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