Triethylamine → (R)-N-methyl-3-(2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yloxy)benzene sulfonamide
Reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].C(N(CC)CC)C.[OH:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][C@@H:27]([NH:32][S:33]([CH:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])[CH2:26]2>C(Cl)Cl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[CH2:28][C@@H:27]([NH:32][S:33]([CH:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])[CH2:26]3)[CH:7]=1)(=[O:5])=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a mixture of the 3-(N-methylsulfamoyl)phenylboronic acid (0.274 mmol, 59 mg), copper (II)acetate (0.137 mmol, 25 mg), triethylamine (0.685 mmol, 96 μL) and 4 Å molecular sieves (100 mg) in DCM (1 mL) was added (R)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.137 mmol, 35 mg) and the resultant mixture stirred at room temperature overnight. The reaction mixture was diluted with DCM (1 mL) before water (0.5 mL) was added and the organic layers separated using hydrophobic frits. The aqueous was extracted with further DCM (1 mL), and the combined organics concentrated using to dryness. The residue was taken up in DMSO and purified by preparative HPLC to give the title compound as a clear film (5.9 mg, 10.1%). MS (ESI): m/z [M−H]− 423.2
Workup
- additionwas added
- customthe organic layers separated
- extractionThe aqueous was extracted with further DCM (1 mL)
- concentrationthe combined organics concentrated
- custompurified by preparative HPLC
Sources & evidence
- ORD record
- ord-e2f61ae4af4c4e0f8b3bd5aec2e45fb5
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633237B2
Reaction notes
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