Trifluoroacetic acid → Methyl[4-(1-methylpiperidin-4-yl)-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl]acetate

HRID 389032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389032
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:35])[CH2:11][S:12][C:13]1[CH:14]=[CH:15][C:16]2[O:25][CH2:24][C:23]3[CH:22]=[CH:21][S:20][C:19]=3[C:18](O)([CH:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[C:17]=2[CH:34]=1.Cl.O1CCOCC1>ClCCl>[CH3:8][O:9][C:10](=[O:35])[CH2:11][S:12][C:13]1[CH:14]=[CH:15][C:16]2[O:25][CH2:24][C:23]3[CH:22]=[CH:21][S:20][C:19]=3[CH:18]([CH:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[C:17]=2[CH:34]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 204431481,4-Dioxane hydrochlorideHCID 86649443Methyl[4-hydroxy-4-(1-methylpiperidin-4-yl)-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl]acetate

Produkt 1

HCID 86649444Methyl[4-(1-methylpiperidin-4-yl)-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl]acetateAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (10 mL) was added to a dichloromethane solution of the compound obtained in Example 23 (5.7 g, 14 mmol), and the mixture was stirred at room temperature overnight. The solvents were distilled off, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2), to give a free compound. Thereafter, 4 mol/L hydrogen chloride-dioxane (8.0 mL, 32 mmol) was added thereto, and the mixture was stirred for 1 hour. The solvents were distilled off under a reduced pressure, and ether was added to the residue to allow crystallization. The precipitated crystals were separated by filtration and dried, to give 4.1 g (69%) of the captioned compound.

Aufarbeitung

  1. distillationThe solvents were distilled off
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)
  3. customto give a free compound
  4. stirringthe mixture was stirred for 1 hour
  5. distillationThe solvents were distilled off under a reduced pressure, and ether
  6. additionwas added to the residue
  7. customcrystallization
  8. customThe precipitated crystals were separated by filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a3b15bdd44f949bd9607610d23418b2e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377967B2

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