Trifluoroacetic acid → HCID 57437813, Verbindung

HRID 2354365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354365
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[NH:7][C:8](=[O:10])[O:9][C:5]=2[CH:4]=1.[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].FC(F)(F)C(O)=O>C1COCC1.CC#N.O>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:7]1[C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[O:9][C:8]1=[O:10])[CH3:21]

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 7748Ethyl bromoacetateHCID 10772CoixolHCID 24758Sodium hydride

Produkt 1

HCID 57437813HCID 57437813, VerbindungAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of 6-methoxy-2-benzoxazolinone (0.78 g, 4.72 mmol) dissolved in 5 mL of anhydrous THF was added to a suspension of sodium hydride (0.208 g of a 60% dispersion in mineral oil, 5.2 mmol) in 10 mL of anhydrous THF at room temperature and stirred for 10 minutes. Then, ethyl bromoacetate (0.629 mL, 5.67 mmol) was added and stirred at room temperature for two hours. HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid) showed that almost all of the starting material (Rt=4.36 min) was gone and that a new peak (Rt=6.0 min) had formed. The reaction was quenched with 2 mL of 4.0M HCl in dioxane. The solvent was removed by rotary evaporation and the residue was adsorbed onto approximately 10 g of silica gel and purified by column chromatography (40 g silica gel 40 um, gradient elution from 100% dichloromethane to 35% methanol/65% dichloromethane over 40 minutes) to give ethyl[6-(methyloxy)-2-oxo-1,3-benzoxazol-3(2H)-yl]acetate (0.96 g, 3.84 mmol, 81%) as a white crystalline solid. MS (ES) m/e 252 [M+H]+.

Aufarbeitung

  1. stirringstirred at room temperature for two hours
  2. customhad formed
  3. customThe reaction was quenched with 2 mL of 4.0M HCl in dioxane
  4. customThe solvent was removed by rotary evaporation
  5. custompurified by column chromatography (40 g silica gel 40 um, gradient elution from 100% dichloromethane to 35% methanol/65% dichloromethane over 40 minutes)

Quellen und Nachweise

ORD-Eintrag
ord-9d33237e732e4c5fac31da4d6f8a191e
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749998B2

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