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Water → tert-butyl{(2S)-1-[4-chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenoxy]propan-2-yl}carbamate

HRID 2178701
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2178701
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]([CH3:21])([CH3:20])[C:16]([F:19])([F:18])[F:17])[CH:9]=1.CS(O[CH2:27][C@@H:28]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH3:29])(=O)=O.O>CN(C)C=O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:29][C@@H:28]([NH:30][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:37])[CH3:36])[CH3:27])=[C:10]([C:15]([CH3:21])([CH3:20])[C:16]([F:17])([F:18])[F:19])[CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 10753379(S)-Methanesulphonic acid 2-Boc-aminopropyl esterHCID 866717284-Chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenol

Produkt 1

HCID 70807897tert-butyl{(2S)-1-[4-chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenoxy]propan-2-yl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Cesium carbonate (2.05 g, 6.28 mmol) was added to a solution of 4-chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenol (C48) (500 mg, 2.10 mmol) in N,N-dimethylformamide (5 mL). (2S)-2-[(tert-Butoxycarbonyl)amino]propyl methanesulfonate (P12) (0.53 g, 2.1 mmol) was added, and the reaction mixture was heated to 60° C. After 30 minutes, additional P12 (0.53 g, 2.1 mmol) was added, and heating was continued for 18 hours. Water (100 mL) was added, and the mixture was extracted with diethyl ether (3×50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Silica gel chromatography (Gradient: 0% to 15% ethyl acetate in heptane) afforded the product as a colorless oil. Yield: 625 mg, 1.58 mmol, 75%.

Aufarbeitung

  1. additionadditional P12 (0.53 g, 2.1 mmol) was added
  2. temperatureheating
  3. waitwas continued for 18 hours
  4. extractionthe mixture was extracted with diethyl ether (3×50 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eb8cedd37a054055b331dcec2b8eb380
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067934B2

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