Trifluoroacetic acid → HCID 178487802, Verbindung

HRID 633806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633806
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][CH:22]2[CH2:36][C:25]3=[C:26]4[C:31](=[N:32][CH:33]=[C:24]3[O:23]2)[CH:30]=[CH:29][C:28]([O:34][CH3:35])=[N:27]4)[CH2:17][CH2:16]1)(C)(C)C>ClCCl>[CH3:35][O:34][C:28]1[CH:29]=[CH:30][C:31]2[C:26]([N:27]=1)=[C:25]1[CH2:36][CH:22]([CH2:21][C@H:18]3[CH2:19][CH2:20][C@H:15]([NH2:14])[CH2:16][CH2:17]3)[O:23][C:24]1=[CH:33][N:32]=2

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 178487805HCID 178487805, Verbindung

Produkt 1

HCID 178487802HCID 178487802, VerbindungAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (821 μL, 10.56 mmol, 15.0 eq) is added at 0° C. to a stirred solution of [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester (300 mg, 0.70 mmol, 1.0 eq) in dichloromethane (12 mL). After 2 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×10 mL) and water (10 mL) and the pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine as an orange viscous oil (190 mg, 82% yield).

Aufarbeitung

  1. extractionthe reaction mixture is extracted with dichloromethane (3×10 mL) and water (10 mL)
  2. additionthe pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3dc1885ed42f4482afe6103137bb24b3
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321788B2

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