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Dichloromethane → ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate

HRID 2193150
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2193150
ClCCl.C(OC([N:11]([CH2:40][C:41]1[CH:50]=[CH:49][C:44]2[O:45][CH2:46][CH2:47][O:48][C:43]=2[CH:42]=1)[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[C:25](/[CH:32]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=3)[CH:23]=[CH:22][C:21]2=[O:39])[CH2:14][CH2:13]1)=O)(C)(C)C.FC(F)(F)C(O)=O>CCCCCC>[O:45]1[C:44]2[CH:49]=[CH:50][C:41]([CH2:40][NH:11][CH:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][N:20]4[C:29]5[C:24](=[C:25](/[CH:32]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=5)[CH:23]=[CH:22][C:21]4=[O:39])[CH2:16][CH2:17]3)=[CH:42][C:43]=2[O:48][CH2:47][CH2:46]1
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Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68193064HCID 68193064, Verbindung

Produkt 1

HCID 86643185ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylateAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058
Hexane
Lösungsmittel

Versuchsvorschrift

To 3 mL of a dichloromethane solution containing 0.15 g of ethyl (2E)-3-(1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate, 3 mL of trifluoroacetic acid was added and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, chloroform and water were added, and adjusted to pH 10 with 20% aqueous sodium hydroxide solution, under ice-cooling. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue thus obtained, hexane was added and the resulting solid was filtered to give 0.12 g of ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate as a light brown solid.

Aufarbeitung

  1. additionwas added
  2. customThe solvent was removed under reduced pressure, chloroform and water
  3. additionwere added
  4. temperaturecooling
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. washwashed sequentially with water and aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customTo the residue thus obtained
  11. filtrationthe resulting solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-00eb3604a16d4aeaa64bc8851409baf4
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329694B2

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