Methyl 2-(3,4,5-trimethoxyphenyl)acetate → HCID 135702888, Verbindung

HRID 566340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566340
[NH2:1][C:2]1[N:6]([CH:7]([CH3:17])[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[C:4]([CH2:18][CH3:19])[C:3]=1[C:20]([NH2:22])=[O:21].CC(C)([O-])C.[K+].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH2:41][C:42](OC)=O)[CH:34]=[C:35]([O:39][CH3:40])[C:36]=1[O:37][CH3:38]>C(O)C>[CH3:40][O:39][C:35]1[CH:34]=[C:33]([CH:32]=[C:31]([O:30][CH3:29])[C:36]=1[O:37][CH3:38])[CH2:41][C:42]1[NH:22][C:20](=[O:21])[C:3]2[C:4]([CH2:18][CH3:19])=[N:5][N:6]([CH:7]([CH3:17])[CH2:8][CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:2]=2[N:1]=1

Komponenten

5

Edukt 3

HCID 11107458Methyl 2-(3,4,5-trimethoxyphenyl)acetateHCID 21266063HCID 21266063, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 135702888HCID 135702888, VerbindungAusbeute 41,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

400 mg (1.4mmol) of 5-amino-3-ethyl-1-(1-methyl-4-phenyl-butyl)-1H-pyrazole-4-carboxamide, 750 mg (6.7 mmol) of potassium tert-butoxide and 720 mg (3.0 mmol) of methyl 3,4,5-trimethoxy-phenylacetate are refluxed for 16 hours in 10 ml of ethanol. After the solvent has been removed, the mixture is acidified with 1N HCl, extracted 3 times with dichloromethane, the organic phase is dried over sodium sulphate and the solvent is removed in vacuo. Purification by chromatography gives 286 mg (40%) of a solid, Rf=0.62 (ethyl acetate/cyclohexane=2:1).

Aufarbeitung

  1. customAfter the solvent has been removed
  2. extractionextracted 3 times with dichloromethane
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. customPurification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-96aa96c273a2492980589977139bd191
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174884B1

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