Water → 3-(4-Ethoxy-2-oxocyclohex-3-enyl)propyl 2-(methylamino)benzoate

HRID 77270

Reaktionsgleichung

Reaktionsgleichung von HRID 77270
[CH2:1]([O:3][C:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH2:12][OH:13])[C:6](=[O:14])[CH:5]=1)[CH3:2].CCN(CC)CC.[CH3:22][N:23]1C(=O)O[C:26](=[O:27])[C:25]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:24]12.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:22][NH:23][C:24]1[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=1[C:26]([O:13][CH2:12][CH2:11][CH2:10][CH:7]1[CH2:8][CH2:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]1=[O:14])=[O:27]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 25160N-Methylisatoic anhydrideHCID 252417513-Ethoxy-6-(3-hydroxypropyl)cyclohex-2-enone

Produkt 1

HCID 252417523-(4-Ethoxy-2-oxocyclohex-3-enyl)propyl 2-(methylamino)benzoateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Alcohol 3 (180 mg, 0.89 mmol), NEt3 (0.56 mL) and catalytic DMAP were added to a solution of N-methylisatoic anhydride (220 mg, 0.89 mmol) in dry DMF (2.0 mL) at rt. After stirring overnight, the solution was warmed to 65° C. for 3 h. After cooling to rt, water was added and this mixture was extracted with ethyl acetate (5×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated to give the crude product, which was purified by flash column chromatography to afford 87.0 mg (45% yield) of 4 as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.85 (1H, m), 7.33 (1H, m), 6.56 (2H, m), 5.27 (1H, s), 4.22 (2H, t, J=5.2 Hz), 3.85 (2H, q, J=7.0 Hz), 2.86 (3H, s), 2.39 (2H, t, J=5.3 Hz), 2.04-1.41 (7H, m), 1.31 (3H, t, J=7.0 Hz); 13C NMR (75 MHz, CDCl3) δ 201.1, 176.8, 168.7, 151.7, 134.7, 131.7, 115.0, 111.3, 110.6, 102.5, 101.9, 64.7, 64.5, 64.3, 44.9, 30.0, 28.2, 26.6, 26.5, 26.4, 14.3; ESI MS m/z 354 (M++Na+).

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. extractionthis mixture was extracted with ethyl acetate (5×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product, which
  8. customwas purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-958ff28899cb4cf1895dc65cd340913b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841132B2

Verknüpfte Notizen

Wird geladen…