Sodium Carbonate → N-{4-chloro-6-(N,N-dihexylamino)-1,3,5-triazin-2-yl}phenylalanine ethyl ester

HRID 1070442

Reaktionsgleichung

Reaktionsgleichung von HRID 1070442
Cl.[CH2:2]([O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:7])[CH3:3].[Cl:16][C:17]1[N:22]=[C:21](Cl)[N:20]=[C:19]([N:24]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(OCC)(=O)C.O>[CH2:2]([O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH:7][C:21]1[N:22]=[C:17]([Cl:16])[N:18]=[C:19]([N:24]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:20]=1)[CH3:3]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 105206134,6-Dichloro-N,N-dihexyl-1,3,5-triazin-2-amine

Produkt 1

HCID 57120797N-{4-chloro-6-(N,N-dihexylamino)-1,3,5-triazin-2-yl}phenylalanine ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

L-phenylalanine ethyl ester hydrochloride (1.0 g, 4.4 mmol) was added to a mixture of 2,4-dichloro-6-dihexylamino-1,3,5-triazine (1.5 g, 4.5 mmol) and sodium carbonate (0.92 g, 8.7 mmol) in acetonitrile (40 mL). The reaction mixture was heated to reflux for 16 h and then allowed to col to ambient temperature. The mixture was diluted with ethyl acetate and water. The phases were separated and the organic phase was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude material was purified by flash column chromatography through silica gel (elution with chloroform) to afford N-{4-chloro-6-(N,N-dihexylamino)-1,3,5-triazin-2-yl}phenylalanine ethyl ester. Anal. Calcd. for C26H40ClN5O2: C, 63.72; H, 8.23; N 14.29. Found: C, 63.67; H, 8.06; N 14.24.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. customto col to ambient temperature
  4. customThe phases were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash column chromatography through silica gel (elution with chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-9e5929ea5d5344b1afa90324bcab763a
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903088B2

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