Ethanol → HCID 178445797, Verbindung

HRID 1802103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802103
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[C:13]([C:29]([F:32])([F:31])[F:30])=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25]C(=O)[NH:23]2)[N:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(O)C.[OH-].[Li+].O>>[NH2:23][C@@:22]([C:17]1[N:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]3[CH2:7][CH2:6][C@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][CH2:9]3)[C:13]=2[C:29]([F:32])([F:30])[F:31])[N:18]=1)([CH3:28])[CH2:26][OH:25]

Komponenten

5

Edukt 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67409191(R)-4-(6-(trans-4-tert-Butylcyclohexyloxy)-5-(trifluoromethyl)quinazolin-2-yl)-4-methyloxazolidin-2-one

Produkt 1

HCID 178445797HCID 178445797, VerbindungAusbeute 90 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(R)-4-[6-(4-tert-Butyl-cyclohexyloxy)-5-trifluoromethyl-quinazolin-2-yl]-4-methyl-oxazolidin-2-one (180.0 mg, 0.0003987 mol) was dissolved in ethanol (7 mL, 0.1 mol), followed by 4 M lithium hydroxide in water (3 mL, 0.01 mol). The reaction mixture was then heated at 80° C. for 2 hours. All solvent was removed. The solid was extracted with DCM, and organic layers were dried over Na2SO4. Removal of solvent gave a pure product (152 mg, 90%). 1H NMR (MeOD) δ: 9.73 (s, 1H), 8.24 (d, J=9.3 Hz, 1H), 8.05 (d, J=9.5 Hz, 1H), 4.50-4.68 (m, 1H), 4.11 (d, J=11.0 Hz, 1H), 3.84 (d, J=11.0 Hz, 1H), 2.22 (d, J=10.8 Hz, 2H), 1.92 (d, J=13.1 Hz, 2H), 1.61 (s, 3H), 1.43-1.58 (m, 2H), 1.18-1.35 (m, 2H), 1.04-1.18 (m, 1H), 0.91 (s, 9H). MS (M+1): 426.30.

Aufarbeitung

  1. customAll solvent was removed
  2. extractionThe solid was extracted with DCM, and organic layers
  3. dry with materialwere dried over Na2SO4
  4. customRemoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-92a1f3c85a8c4178ac9be4bcfce4c865
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349849B2

Notizen zur Reaktion

Wird geladen…