Hydrogen Peroxide → n-{3-[4-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]propyl}(phenylmethoxy)carboxamide
Reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:17])[CH2:9][NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:4][CH:3]=1.[C:18]1([CH2:24][O:25][C:26]([NH:28][CH2:29][CH:30]=[CH2:31])=[O:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.[OH-].[Na+].OO>Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:17][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH2:31][CH2:30][CH2:29][NH:28][C:26]([O:25][CH2:24][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:27])=[CH:3][CH:4]=1)[CH2:9][NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Scheme Vc, step A: 2-(4-Iodophenyl) propyl isopropylsulfonamide (1.5 g, 4.1 mmol), (phenylmethoxy)-N-prop-2-enylcarboxamide (0.94 g, 4.9 mmol, prepared in example 8), 9-BBN dimer (0.8 g, 3.28 mmol), [1,1′bis(diphenylphosphino)-ferrocene] dichloropalladium (II), PdCl2(dppf) (0.17 g, 0.2 mmol), 3N sodium hydroxide (3 mL), and pH=7 buffer: hydrogen peroxide (2:1, 15 mL) were combined in a manner analogous to the procedure described in example 6 to provide the intermediate title compound, N-{3-[4-(1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]propyl}(phenylmethoxy)carboxamide, (1.74 g, 99%). Electron spray M.S. 431 (M*−H).
Sources & evidence
- ORD record
- ord-c5ba87990ed4416182880112de0bcb1e
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06703425B2
Reaction notes
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