Water → HCID 67040558, Verbindung

HRID 604532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604532
[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:29][C:30](=[O:32])[CH3:31])([CH3:28])[CH2:20][CH2:21][C:22]1[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)(=[O:16])[CH3:15].C([O:36][CH2:37][CH3:38])(=O)C.O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:14]([O:17][CH2:18][C@@:19]([NH:29][C:30](=[O:32])[CH3:31])([CH3:28])[CH2:20][CH2:21][C:22]1[N:23]([CH3:27])[C:24]([C:11]([O:12][C:37](=[O:36])[CH2:38][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 66672660HCID 66672660, Verbindung

Produkt 1

HCID 67040558HCID 67040558, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Thionyl chloride (9.0 mL, 123 mmol) and N,N -dimethylformamide (50 μL) were added to a solution of 4-(4-methylphenyl)butyric acid (11.0 g, 62.0 mmol) in benzene (220 mL) and the mixture was stirred at 80° C. for 2 hours. After cooling the mixture to room temperature, the solvent was evaporated under reduced pressure to obtain 5-(4-methylphenyl)butyric chloride. A solution of 4-dimethylaminopyridine (15.2 g, 124 mmol) and 4-(4-methylphenyl)butyric chloride (12.2 g, 62.0 mmol) in toluene (50 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-(1-methylpyrrol-2-yl)butane (5.00 g, 18.8 mmol) obtained in Reference example 1 in toluene (150 mL) and the mixture was stirred at 110° C. for 48 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 and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (5.15 g, yield: 47%).

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. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-5c5646f845a04cfc80ff7163abd49060
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910617B2

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