Dimethylformamide → N-[(1RS,2SR)-1-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-2-hydroxyethyl]-5-fluoro-1-naphthamide

HRID 1610735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610735
[NH2:1][CH:2]([CH2:12]CC1C=CC(C(C)(C)C)=CC=1)[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)[OH:4].[F:24][C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][CH:29]=[C:30]2[C:35]([OH:37])=O.O.ON1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2N=N1.Cl.C(N=C=N[CH2:55][CH2:56][CH2:57]N(C)C)C.[CH3:61]N(C)C=O>C(OCC)(=O)C>[C:56]([C:43]1[CH:48]=[CH:47][C:46]([CH2:12][CH:2]([NH:1][C:35]([C:30]2[C:31]3[C:26](=[C:25]([F:24])[CH:34]=[CH:33][CH:32]=3)[CH:27]=[CH:28][CH:29]=2)=[O:37])[CH:3]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[OH:4])=[CH:45][CH:44]=1)([CH3:57])([CH3:61])[CH3:55]

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 149872365-Fluoronaphthalene-1-carboxylic acidHCID 22261419(1RS,2RS)-2-amino-3-[4-(tert-butyl)benzyl]-1-(4-fluorophenyl)propan-1-ol

Produkt 1

HCID 22261768N-[(1RS,2SR)-1-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-2-hydroxyethyl]-5-fluoro-1-naphthamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (1RS,2RS)-2-amino-3-[4-(tert-butyl)benzyl]-1-(4-fluorophenyl)propan-1-ol (0.22 g, 0.70 mmol) in N,N-dimethylformamide (10 ml) were added 5-fluoronaphthalene-1-carboxylic acid (122 mg, 0.64 mmol) and 1-hydroxybenzotriazole monohydrate (108 mg, 0.70 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (134 mg, 0.70 mmol) was finally added. The mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) and recrystallization (hexane-ethyl acetate) to give N-[(1RS,2SR)-1-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-2-hydroxyethyl]-5-fluoro-1-naphthamide (153 mg, 50%) as colorless crystals.

Aufarbeitung

  1. additionwas finally added
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) and recrystallization (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-93eecff562004d17921a07f73e3a2eb6
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

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