Water → HCID 86592016, Verbindung

HRID 1785881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1785881
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@H:11]([N:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19](=[O:22])[CH2:20]C)[CH2:10][C@@H:9]2[CH3:29])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41].O>CN(C)C=O>[CH3:43][O:42][C:40](=[O:41])[CH:39]([NH:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@H:11]([N:18]([C:19](=[O:22])[CH3:20])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:10][C@@H:9]2[CH3:29])=[O:7])=[CH:4][CH:3]=1)[CH3:44]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 86592010HCID 86592010, Verbindung2×

Produkt 1

HCID 86592016HCID 86592016, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(±)-Cis-2-{4-[4-(acetyl-phenyl-amino)-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl]-phenylamino}-propionic acid methyl ester was prepared from (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. A mixture of (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide (210 mg, 0.53 mmol), potassium carbonate (123 mg, 0.89 mmol), and methyl 2-bromopropionate (70 uL, 0.63 mmol) in dry dimethylformamide (2 mL) was heated at 100° C. for 6 h, then cooled to room temperature and stirred with 20 ml water until all of the salts dissolved. The aqueous layer was separated and was extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting oil was purified by silica gel chromatography, eluting with (97:3 methylene chloride/methanol) to afford the title compound (220 mg, 87%).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. dissolutiondissolved
  3. customThe aqueous layer was separated
  4. extractionwas extracted with ethyl acetate
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting oil was purified by silica gel chromatography
  10. washeluting with (97:3 methylene chloride/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-4ac644dd7a2141dea55bcae060251f8c
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504508B2

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