Ethanol → HCID 178464723, Verbindung

HRID 1036404

Reaktionsgleichung

[CH3:1][C@@:2]1([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]4[CH2:24][CH2:23][C@@H:22]([CH3:25])[CH2:21][CH2:20]4)[CH:14]=3)[CH:9]=2)[CH2:6][O:5]C(=O)[NH:3]1.C(O)C.O.[OH-].[Li+]>O>[NH2:3][C@@:2]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]3[CH2:20][CH2:21][C@@H:22]([CH3:25])[CH2:23][CH2:24]3)[CH:14]=2)[CH:9]=1)([CH3:1])[CH2:6][OH:5]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of (R)-4-Methyl-4-[6-(cis4-methyl-cyclohexyloxy)-naphthalen-2-yl]-oxazolidin-2-one (0.4420 g, 0.001302 mol) in ethanol (5.00 mL, 0.0856 mol) in a capped 40 mL vial was added 4.2 M Lithium hydroxide, monohydrate in water (2.8 mL). The mixture was heated overnight at 80° C. TLC analysis showed the reaction was complete. The mixture was concentrated to dryness under vacuum. Methylene chloride (5 mL) and water (5 mL) were added and the layers were separated (2×). The organic layer was concentrated under vacuum and purified by HPLC to give 0.0233 g of the title compound (6% yield). MS: m/z=297.29 [M−NH2]+. 1H NMR (400 MHz, MeOD) δ 0.98 (d, J=6.02 Hz, 3H), 1.40-1.51 (m, 2H), 1.51-1.60 (m, 3H), 1.64-1.74 (m, 2H), 1.79 (s, 3H), 2.03-2.14 (m, 2H), 3.83 (d, J=11.55 Hz, 1H), 3.93 (d, J=11.55 Hz, 1H), 4.69-4.77 (m, 1H), 7.23 (dd, J=8.91, 2.38 Hz, 1H), 7.27 (d, J=2.51 Hz, 1H), 7.53 (dd, J=8.78, 2.01 Hz, 1H), 7.79-7.89 (m, 3H)

Aufarbeitung

concentrationThe mixture was concentrated to dryness under vacuum
additionMethylene chloride (5 mL) and water (5 mL) were added
customthe layers were separated (2×)
concentrationThe organic layer was concentrated under vacuum
custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag: ord-e4605061053247c280ea13972fb55ad0
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08546359B2

Verknüpfte Notizen

Wird geladen…