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Water → (S)-4-[2-Hydroxy-3-([4-(4-carbamoylphenoxy)phenyl]-2-methylpropylamino)propoxy]carbazole

HRID 2119837
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2119837
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.NC(C)(C)C[C:22]1[CH:37]=[CH:36][C:25]([O:26][C:27]2[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[O:32])=[CH:29][CH:28]=2)=[CH:24][CH:23]=1.O>C(O)(=O)C.CO>[OH:1][C@@H:2]([CH2:3][N:11]([C:22]1[CH:23]=[CH:24][C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]([C:31](=[O:32])[NH2:33])=[CH:34][CH:35]=2)=[CH:36][CH:37]=1)[CH2:10][CH:18]([CH3:6])[CH3:17])[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazoleHCID 118329614-(4-(2-Amino-2-methylpropyl)phenoxy)benzamide2×

Produkt 1

HCID 53754997(S)-4-[2-Hydroxy-3-([4-(4-carbamoylphenoxy)phenyl]-2-methylpropylamino)propoxy]carbazoleAusbeute 174,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Katalysator
HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A stirred mixture of (S)-(+)-4-(oxiranylmethoxy)-carbazole (7.50 g, 31.3 mmol), 4-(4-(2-amino-2-methylpropyl)-phenoxy)benzamide (17.82 g, 62.67 mmol), acetic acid (0.10 g, 1.7 mmol), water (10 mL) and methanol (260 mL) was heated to 60° C. for 22.7 hrs. The mixture was cooled and concentrated in vacuo to an oil. The concentrate was taken up in ethyl acetate (250 mL) and partitioned with water (100 mL). The organic layer was then extracted with a solution of 25 mL 1N HCl (25 mL) in water (35 mL). A white precipitate formed during the extraction was mostly 4-(4-(2-amino-2-methylpropyl)-phenoxy)benzamide and was removed by filtration of the two phase mixture. The organic layer was extracted two times with a solution of 1N HCl (3 mL) in water (50 mL). The ethyl acetate layer was stripped to an oily residue. The crude product was purified by flash chromatography with 416 g 230-400 silica gel and eluting with ethyl acetate then 10:1-3 ethyl acetate:ethanol gradient. Concentration of the appropriate fractions and drying under vacuum gave 14.31 g (87.2%) of the desired product as a foamy white solid. 1H NMR was consistent with the desired compound.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo to an oil
  3. custompartitioned with water (100 mL)
  4. extractionThe organic layer was then extracted with a solution of 25 mL 1N HCl (25 mL) in water (35 mL)
  5. customA white precipitate formed during the extraction
  6. customwas removed by filtration of the two phase mixture
  7. extractionThe organic layer was extracted two times with a solution of 1N HCl (3 mL) in water (50 mL)
  8. customThe crude product was purified by flash chromatography with 416 g 230-400 silica gel
  9. washeluting with ethyl acetate
  10. customConcentration of the appropriate fractions and drying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9b746486791b4efbb101ef4663d8f871
Quelldatensatz
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06686372B2

Notizen zur Reaktion

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