(3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide → (3R,4R)-N-hydroxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide
Reaktionsgleichung
C([O:5][NH:6][C:7]([C@:9]1([CH3:38])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:8])(C)(C)C>FC(F)(F)C(O)=O>[OH:5][NH:6][C:7]([C@:9]1([CH3:38])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:8]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The (3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide (0.52 g, 0.96 mmol) from Step 10 was stirred in neat trifluoroacetic acid (3 mL) at 40° C. for 3.5 h. The reaction mixture was then concentrated in vacuo and chased with methanol. The residue was then stirred in ethyl acetate (100 mL) and saturated NaHCO3 (50 mL) for 15 min. The organic layer was washed with water (50 mL), then with brine (50 mL), dried over MgSO4, and concentrated. The residue was purified by chromatography on silica eluting with 5-8% MeOH/CH2Cl2 to yield 140 mg (30%) of (3R,4R)-N-hydroxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide as an off-white solid. In addition, 35% of the starting material was recovered. HRMS: calcd for C24H27N3O6S+H+, 486.16933; found (ESI-FT-MS, [M+H]+1), 486.1695