Trifluoroacetic acid → HCID 178485960, Verbindung

HRID 25596

Reaktionsgleichung

Reaktionsgleichung von HRID 25596
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:5][CH2:4]1.FC(F)(F)C(O)=O.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)=[O:28].CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([O:29][C:27]([N:2]([CH3:1])[C@H:3]2[CH2:8][CH2:7][C@H:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:5][CH2:4]2)=[O:28])=[CH:31][CH:32]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 178484796HCID 178484796, Verbindung

Produkt 1

HCID 178485960HCID 178485960, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 245 mg (0.53 mmol) trans-Methansulfonic acid 5-(4-methyl amino-cyclohexyl)-pentyl ester.trifluoroacetic acid salt and 143.5 mg (0.75 mmol) 4-chlorophenyl chloroformate in 4 ml dioxane, was added at RT 1.54 ml (3.12 mmol) Hünig's base. The mixture was stirred for 1 h, then extracted with EtOAc/1N HCl and water. The organic phases were concentrated under reduced pressure and purified by chromatography on silica gel with EtOAc/hexane 1:3 to yield 167 mg (73%, 2 steps) of pure trans-Methanesulfonic acid 5-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-pentyl ester, MS: 432 (MH+, 1Cl).

Aufarbeitung

  1. extractionextracted with EtOAc/1N HCl and water
  2. concentrationThe organic phases were concentrated under reduced pressure
  3. custompurified by chromatography on silica gel with EtOAc/hexane 1:3

Quellen und Nachweise

ORD-Eintrag
ord-3dd1e7cf9709491f93dec68a613b9798
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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