Tetrahydrofuran → 5-Tert-butyl-3-methanesulfonylamino-2-methoxy-benzoic acid methyl ester
Reaction equation
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]Participants
5
Procedure
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).
Workup
- customthe solvent was removed
- customthe resulting orange semi-solid triturated with MTBE (3×10 mL)
- customwas bubbled through, 60 mg of Pd(OAc)2
- additionwas added
- stirringthe mixture was stirred with continuous CO bubbling for 1 h
- filtrationThe solution was filtered
- concentrationconcentrated
- custompurified by chromatography (0 to 50% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-55957b6ca7bf4e2cb76c43419e25eaea
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531560B2
Reaction notes
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