Hydrochloric Acid → HCID 178422083, Verbindung

HRID 46131

Reaktionsgleichung

Reaktionsgleichung von HRID 46131
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)([CH3:15])[C:12](=[O:14])[N:13]=1.Cl>CCOC(C)=O>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH3:15])([CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:12](=[O:14])[N:13]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 178451850tert-butyl 4-[[2-[[(2S)-2-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]methyl]piperidine-1-carboxylate

Produkt 1

HCID 178422083HCID 178422083, VerbindungAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 4-((2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)methyl)piperidine-1-carboxylate (1.42 g, 3.37 mmol, 1.0 eq) in 50 mL of a 4.7 M HCl solution in EtOAc was stirred at roomtemperature. After 4 h, the reaction mixture was concentrated in vacuo. Aqueous Na2CO3 (2.0 M, 20 mL) was then added, and water was removed in vacuo. The residue was then triturated with 10% MeOH—CH2Cl2 (6×100 mL), and the combined triturating solution were concentrated in vacuo. The crude product was dissolved in CH2Cl2, filtered, and concentrated in vacuo to afford the title compound as a light orange solid (1.08 g). MS (ESI, pos. ion) m/z: 322 (M+H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionAqueous Na2CO3 (2.0 M, 20 mL) was then added
  3. customwater was removed in vacuo
  4. customThe residue was then triturated with 10% MeOH—CH2Cl2 (6×100 mL)
  5. customthe combined triturating solution
  6. concentrationwere concentrated in vacuo
  7. dissolutionThe crude product was dissolved in CH2Cl2
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-54fa3821d91d491a9c7e48593ed91740
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541592B2

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