Methanol → N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamide

HRID 2354255Notes

Reaction equation

HRID 2354255 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[C:19]([CH3:28])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29].[C:33]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:32][C:2]([CH3:1])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH3:33])[S:24]([CH3:27])(=[O:26])=[O:25])=[C:19]([CH3:28])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11224956N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-methanesulfonamide

Product 1

HCID 11155721N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamideYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-methanesulfonamide (230 mg, 0.5 mmol), triphenyl phosphine (197 mg, 0.75 mmol), MeOH (0.03 mL, 0.75 mmol), and THF (10 mL) is added diethylazodicarboxylate (0.12 mL, 0.75 mmol) and stirred overnight. The reaction is concentrated and chromatographed (0% to 25% EtOAc/Hex) to give the title compound (180 mg, 76%).

Workup

  1. concentrationThe reaction is concentrated
  2. customchromatographed (0% to 25% EtOAc/Hex)

Sources & evidence

ORD record
ord-724955c5fd3c4eba953491d69c55eddc
Source dataset
uspto-grants-2010_07
Patent number
US07750184B2

Reaction notes

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