Methyl iodide → Methyl 2-[{[4-(2,3-butadienyloxy)phenyl]sulfonyl}(methyl)amino]-3-methylbutanoate

HRID 1180543Notes

Reaction equation

HRID 1180543 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH:2]=[C:3]=[CH2:4].[H-].[Na+].[CH3:26]I>O1CCCC1>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]([CH3:26])[CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:10][CH:11]=1)[CH:2]=[C:3]=[CH2:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 85826249Methyl 2-({[4-(2,3-butadienyloxy)phenyl]sulfonyl}amino)-3-methylbutanoate

Product 1

HCID 85826253Methyl 2-[{[4-(2,3-butadienyloxy)phenyl]sulfonyl}(methyl)amino]-3-methylbutanoateYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of product from Example 11 (400 mg, 1.18 mmol) in tetrahydrofuran (10 ml) was added to a suspension of 60% sodium hydride (57 mg, 1.42 mmol) in tetrahydrofuran (2 ml) and the resulting mixture was stirred for 30 minutes, at which time methyl iodide (335 mg, 2.36 mmol) was added. The resulting mixture was stirred for 15 hours and partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate and the crude residue was purified by flash chromatography to give 350 mg (84%) of the product.

Workup

  1. additionwas added
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2e0ffc368bec4fb18e068628a04d0a62
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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