Water → HCID 67040326, Verbindung

HRID 604537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604537
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12])=[CH:4][CH:3]=1.[C:14]([O:17][CH2:18][C@@:19]([NH:30][C:31](=[O:33])[CH3:32])([CH2:28][CH3:29])[CH2:20][CH2:21][C:22]1[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)(=[O:16])[CH3:15].C([O:37][CH2:38][CH3:39])(=O)C.O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:14]([O:17][CH2:18][C@@:19]([NH:30][C:31](=[O:33])[CH3:32])([CH2:28][CH3:29])[CH2:20][CH2:21][C:22]1[N:23]([CH3:27])[C:24]([C:11]([O:12][C:38](=[O:37])[CH2:39][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:25][CH:26]=1)(=[O:16])[CH3:15]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 231601094-(4-Methylphenyl)butanoyl chlorideHCID 67040053HCID 67040053, Verbindung

Produkt 1

HCID 67040326HCID 67040326, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A solution of 4-dimethylaminopyridine (1.17 g, 11.8 mmol) and 4-(4-methylphenyl)butyric chloride (1.06 g, 5.90 mmol) in toluene (5 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-ethyl-4-(1-methylpyrrol-2-yl)butane (444 mg, 1.60 mmol) obtained in Reference example 2 in toluene (15 mL) and the mixture was stirred at 110° C. for 72 hours. The temperature of the mixture was returned to room temperature and ethyl acetate and water were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (377 mg, yield: 40%).

Aufarbeitung

  1. customwas returned to room temperature
  2. customto separate it
  3. customThe thus obtained organic phase was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous NaCl solution and dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f281ec75072c4c5dbdaebfe0288aea8a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910617B2

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