Methyl morpholine oxide → 4-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}-N-(2-methanesulfonylethyl)-2-methylbenzamide

HRID 230816Notes

Reaction equation

HRID 230816 reaction equation
[CH2:1]([C:3]([C:21]1[CH:35]=[CH:34][C:24]([C:25]([NH:27][CH2:28][CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:26])=[C:23]([CH3:36])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].C[N+]1([O-])CCOCC1>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:18][C:15]([CH3:16])([CH3:17])[C:14](=[O:19])[CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:3]([C:21]2[CH:35]=[CH:34][C:24]([C:25]([NH:27][CH2:28][CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:26])=[C:23]([CH3:36])[CH:22]=2)([CH2:1][CH3:2])[CH2:4][CH3:5])=[CH:7][C:8]=1[CH3:20]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 577634394-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethylbutoxy)-3-methylphenyl]propyl}-N-(2-methanesulfonylethyl)-2-methylbenzamide

Product 1

HCID 103692604-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}-N-(2-methanesulfonylethyl)-2-methylbenzamideYield 76%

Reagents, catalysts & solvents 1

HCID 178419074HCID 178419074, compoundCatalyst

Procedure

Using a procedure analogous to Example 13C, from 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethylbutoxy)-3-methylphenyl]propyl}-N-(2-methanesulfonylethyl)-2-methylbenzamide, Example 14, (0.08 g, 0.16 mmol), NMO (27 mg, 0.24 mmol), and TPAP (2.8 mg, 0.08 mmol) are reacted for 1 h to give the title compound (0.06 g, 76%).

Sources & evidence

ORD record
ord-cb29838849f441ad82187c71a8f73a1c
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

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