Dichloromethane → (2S)-N-[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl]-N,4-dimethyl-2-(methylamino)pentanamide hydrochloride

HRID 2374824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2374824
FC(F)(F)C(O)=O.[CH:8]1[C:18]2[CH:17]=[CH:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[C:13](=[CH:23][CH2:24][CH2:25][N:26]([CH3:43])[C:27]([C@@H:29]([N:34](C)[C:35](=O)OC(C)(C)C)[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:28])[C:12]=2[CH:11]=[CH:10][CH:9]=1.[Cl:44]CCl>>[ClH:44].[CH:19]1[C:15]2[CH:16]=[CH:17][C:18]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13](=[CH:23][CH2:24][CH2:25][N:26]([CH3:43])[C:27](=[O:28])[C@@H:29]([NH:34][CH3:35])[CH2:30][CH:31]([CH3:33])[CH3:32])[C:14]=2[CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59853865t-butyl (1S)-1-{[[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl] (methyl) amino]carbonyl}-3-methylbutyl(methyl)carbamate

Produkt 1

HCID 68420933(2S)-N-[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl]-N,4-dimethyl-2-(methylamino)pentanamide hydrochloride

Versuchsvorschrift

5 ml of dichloromethane and 2.5 ml of trifluoroacetic acid were added to 169 mg (0.35 mmol) of t-butyl (1S)-1-{[[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl](methyl)amino]carbonyl}-3-methylbutyl(methyl)carbamat e, and they were stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. 1 N aqueous sodium hydroxide solution was added thereto to make it basic. After extracting with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was dissolved in 5 ml of 1,4-dioxane. 4 N hydrochloric acid/1,4-dioxane solution was added to the obtained solution. The resultant mixture was concentrated under reduced pressure to obtain the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. addition1 N aqueous sodium hydroxide solution was added
  3. extractionAfter extracting with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 5 ml of 1,4-dioxane
  7. addition4 N hydrochloric acid/1,4-dioxane solution was added to the obtained solution
  8. concentrationThe resultant mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a57687a85e8940928659a1e826ef81aa
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462630B2

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