Reaktionsgleichung
C(N[C:6](=[O:38])[C:7]([NH:34]C(=O)C)([CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=2)[CH2:23][CH2:22]1)[CH2:8][CH2:9][CH2:10][CH2:11][B:12]1[O:16]C(C)(C)C(C)(C)[O:13]1)(C)(C)C.[OH2:39]>Cl>[NH2:34][C:7]([CH:21]1[CH2:22][CH2:23][N:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=2)[CH2:25][CH2:26]1)([CH2:8][CH2:9][CH2:10][CH2:11][B:12]([OH:13])[OH:16])[C:6]([OH:38])=[O:39]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 2-acetylamino-2-(5′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)hexanoic acid, tert-butylamide (1.07 g) in 6 N HCl (20 mL) was stirred at 90° C. for 1 day. After cooling to room temperature, the reaction mixture was transferred to a separatory funnel, diluted with deionized water (10 mL) and washed with dichloromethane (3×). The aqueous layer was frozen in liquid nitrogen and lyophilized to give title compound as a white solid (590 mg, 82%); 1H NMR (D2O, 300 MHz) δ 8.00 (d, J=2.5 Hz, 1H), 7.47 (dd, J1=9.0 Hz, J2=2.5 Hz, 1H), 6.79 (d, J=9 Hz, 1H), 4.42 (d, J=13.5 Hz, 1H), 4.32 (d, J=13 Hz, 1H), 2.79 (t, J=12 Hz, 2H), 2.06 (m, 1H), 1.78-1.94 (m, 3H), 1.55-1.70 (m, 2H), 1.43 (m, 4H), 1.30 (m, 1H) and 0.82 (t, J=7 Hz, 2H); MS (+CI): m/z for C16H25BClN3O4: expected 369.2. found 370.2 (M+H)+, 352.23 (M+H−H2O)+.
Aufarbeitung
- customthe reaction mixture was transferred to a separatory funnel
- washwashed with dichloromethane (3×)
- temperatureThe aqueous layer was frozen in liquid nitrogen
Quellen und Nachweise
- ORD-Eintrag
- ord-e95bcd74dab44e688a6a090b63c66587
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09040703B2
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