4-Methylmorpholine → HCID 178450149, Verbindung

HRID 1270829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270829
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([NH:17][C:18]([O:20][CH2:21][CH:22]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])[C:14](O)=[O:15])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[C:50]1([C:56]2[N:57]=[C:58]([CH:61]3[CH2:70][C:69]4[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=4)[CH2:63][NH:62]3)[NH:59][CH:60]=2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>ClCCl>[CH:24]1[C:23]2[CH:22]([CH2:21][O:20][C:18](=[O:19])[NH:17][CH:13]([CH2:12][C:9]3[CH:8]=[CH:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:11][CH:10]=3)[C:14](=[O:15])[N:62]3[CH:61]([C:58]4[NH:59][CH:60]=[C:56]([C:50]5[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=5)[N:57]=4)[CH2:70][C:69]4[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=4)[CH2:63]3)[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]=2[CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 1001122-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoic acidHCID 178420112HCID 178420112, Verbindung

Produkt 1

HCID 178450149HCID 178450149, VerbindungAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-(4-tert-Butoxy-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (1.93 g, 4.2 mmol) was dissolved in dichloromethane (100 mL), cooled to 0° C., then N-methyl-morpholine (0.42 g, 4.2 mmol) was added neat followed by isobutyl chloroformate (0.52 mL, 4 mmol). After 1.25 hour 3-(4-phenyl-1H-imidazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline (1.10 g, 4 mmol) was added neat and the reaction was allowed to warm to room temperature. After 16 hours the reaction was extracted with water, then saturated NaHCO3, dried over Na2SO4, filtered, and concentrated under reduced pressure to give 2.53 g (88%) of brown foam desired product {1-(4-tert-butoxy-benzyl)-2-oxo-2-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester, which was used without further purification. (LC/MS; Measured MW (MH+): 717)

Aufarbeitung

  1. temperatureto warm to room temperature
  2. extractionAfter 16 hours the reaction was extracted with water
  3. dry with materialsaturated NaHCO3, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5dd0378a82ec4e4fa6630b9b477abd5f
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202381B2

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