Tetrahydrofuran → 5-Tert-butyl-3-methanesulfonylamino-2-methoxy-benzoic acid methyl ester

反応式

N[C:2]1[C:3]([O:17][CH3:18])=[C:4]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.[H+].[B-](F)(F)(F)F.N([O:27][CH2:28]CC(C)C)=O.C1C[O:36][CH2:35]C1>>[CH3:35][O:36][C:28](=[O:27])[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:3]=1[O:17][CH3:18]

参加物

反応物 4

HCID 8028Tetrahydrofuran

HCID 8053Isoamyl Nitrite

HCID 28118Tetrafluoroboric acid

HCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

生成物 1

HCID 576788635-Tert-butyl-3-methanesulfonylamino-2-methoxy-benzoic acid methyl ester

実験手順

To a 0° C. solution of 1.34 g (4.92 mmol) of N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide and 1.3 mL (10 mmol) of 48% aqueous HBF4 in 10 mL of THF was added 586 mg (5 mmol) of isoamyl nitrite. The mixture was stirred 2 h, then the solvent was removed and the resulting orange semi-solid triturated with MTBE (3×10 mL). The resulting residue was taken up in MeOH and while CO was bubbled through, 60 mg of Pd(OAc)2 was added, and the mixture was stirred with continuous CO bubbling for 1 h. The solution was filtered, concentrated, and purified by chromatography (0 to 50% EtOAc in hexanes) to provide the title compound as a white solid (752 mg).