Cesium carbonate → HCID 86722320, Verbindung

HRID 874833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874833
[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:29]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH:42]([CH2:45]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:41][CH2:40]1)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C.O>[C:1]([O:5][C:6]([NH:7][C@@H:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[O:21][CH2:45][CH:42]1[CH2:43][CH2:44][N:39]([C:37]([O:36][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:38])[CH2:40][CH2:41]1)=[O:22])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 218920784-(Toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid benzyl esterHCID 90209372HCID 90209372, Verbindung

Produkt 1

HCID 86722320HCID 86722320, VerbindungAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of (S)-tert-butyl((3-hydroxyphenyl)(phenyl)methyl)carbamate (8.0 g, 26.7 mmol) and cesium carbonate (13.1 g, 37.4 mmol) in DMF (130 ml) was added 4-(toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid benzyl ester (12.94 g, 32.1 mmol). The resulting reaction mixture was stirred at 50° C. for 17 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine (×3), dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography eluting with 0 to 50% ethyl acetate/iso-hexane to afford the title compound (13.7 g, 93%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic extracts were washed with brine (×3)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customthe solvent evaporated at reduced pressure
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 0 to 50% ethyl acetate/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0be0f4c43954424991d5b31e4cbbd015
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980913B2

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