1,2-Dichloroethane → HCID 178442039, Verbindung

HRID 540383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 540383
[CH2:1]([C:6]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][NH:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[NH:16]1[CH:20]=[C:19]([CH2:21][CH2:22][C:23]([NH:25][C@H:26]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:27](O)=[O:28])=[O:24])[N:18]=[CH:17]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[OH-].[Na+]>CN(C=O)C>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][C@@H:26]([NH:25][C:23](=[O:24])[CH2:22][CH2:21][C:19]2[N:18]=[CH:17][NH:16][CH:20]=2)[C:27](=[O:28])[N:8]2[CH2:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:9]2)=[CH:32][CH:33]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 669878863-Pentyl-3-phenylazetidineHCID 178490237HCID 178490237, Verbindung

Produkt 1

HCID 178442039HCID 178442039, VerbindungAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

70 mg (0.345 mmol) of 3-pentyl-3-phenylazetidine and 100 mg (0.315 mmol) of (R)-2-(3-1H-imidazol-4-ylpropionylamino)-3-(4-methoxyphenyl)propanoic acid are solubilized in 1 ml of DMF. 67 mg (0.345 mmol) of EDC and 47 mg (0.345 mmol) of HOBT are added to this solution. The whole is left to stir for 4 hours and is then treated with 1N sodium hydroxide and extracted with dichloromethane. The organic phase is dried over sodium sulphate, filtered and evaporated under pressure. The crude product obtained is purified by silica gel chromatography (eluent 9/1 dichloromethane/methanol). 85 mg of N—[(R)-1-(4-methoxybenzyl)-2-oxo-2-(3-pentyl-3-phenylazetidin-1-yl)ethyl]-3-(1H-imidazol-4-yl)propionamide are obtained in the form of a white powder with a yield of 49%.

Aufarbeitung

  1. waitThe whole is left
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated under pressure
  6. customThe crude product obtained
  7. customis purified by silica gel chromatography (eluent 9/1 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-26e23aea4f5d4a52be3b3590bda60769
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871187B2

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