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2,2,2-Trifluoroethanol → HCID 59347045, Verbindung

HRID 1009128
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1009128
[H-].[Na+].[CH2:3]([OH:8])[C:4]([F:7])([F:6])[F:5].Cl[C:10]1[CH:15]=[C:14]([CH2:16][C@H:17]2[C@@H:21]([CH2:22][OH:23])[O:20][C:19]([CH3:25])([CH3:24])[N:18]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:13]=[CH:12][N:11]=1>CN1C(=O)CCC1.CCOC(C)=O>[OH:23][CH2:22][C@H:21]1[O:20][C:19]([CH3:24])([CH3:25])[N:18]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[C@H:17]1[CH2:16][C:14]1[CH:15]=[CH:10][N:11]=[C:12]([O:8][CH2:3][C:4]([F:7])([F:6])[F:5])[CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 59347033(4S,5S)-Tert-butyl 4-((2-chloropyridin-4-yl)methyl)-5-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate

Produkt 1

HCID 59347045HCID 59347045, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittel
HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

NaH (60% by weight in mineral oil) (0.672 g, 16.8 mmol) was added carefully to trifluoroethanol (20.0 ml, 276 mmol) cooled at 0° C. and then stirred at RT for 30 minutes. The resulting solution is added to (4S,5S)-tert-butyl 4-((2-chloropyridin-4-yl)methyl)-5-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate (0.400 g, 1.12 mmol) dissolved in 10 mL of NMP and the resulting solution was microwaved for 30 minutes fixed at 180° C. The reaction was diluted with EtOAc and washed repeatedly with water. The combined aqueous layers were back extracted with EtOAc and the combined organic layers were washed with water, brine, dried over sodium sulfate and concentrated. The product was purified by silica gel chromatography (2:1 to 1:1 Hexanes/EtOAc) to afford the title compound. MS m/z: 421.3 (100%, M+1).

Aufarbeitung

  1. customthe resulting solution was microwaved for 30 minutes
  2. customfixed at 180° C
  3. washwashed repeatedly with water
  4. extractionThe combined aqueous layers were back extracted with EtOAc
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe product was purified by silica gel chromatography (2:1 to 1:1 Hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-67375c344dca46b6b0a8fb751d42ca99
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07973047B2

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