Water → tert-Butyl {[1-({3-[(dimethylamino)carbonyl]phenyl}sulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}methylcarbamate

HRID 554360Notes

Reaction equation

HRID 554360 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:12][C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([NH:35][CH3:36])=[O:34])[CH:28]=2)(=[O:26])=[O:25])[CH:14]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].I[CH3:38].O>O1CCCC1.CN(C)C=O>[CH3:36][N:35]([CH3:38])[C:33]([C:29]1[CH:28]=[C:27]([S:24]([N:15]2[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:17][C:13]([CH2:12][N:4]([CH3:3])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[CH:14]2)(=[O:26])=[O:25])[CH:32]=[CH:31][CH:30]=1)=[O:34]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66925073tert-Butyl methyl{[1-({3-[(methylamino)carbonyl]phenyl}sulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}carbamate

Product 1

HCID 66924962tert-Butyl {[1-({3-[(dimethylamino)carbonyl]phenyl}sulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}methylcarbamateYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension (3 mL) of sodium hydride (60% in oil, 36 mg) in tetrahydrofuran was added a solution (2 mL) of tert-butyl methyl{[1-({3-[(methylamino)carbonyl]phenyl}sulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}carbamate (240 mg) in N,N-dimethylformamide at room temperature. After stirring at the same temperature for 15 min, iodomethane (106 mg) was added, and the mixture was stirred for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1) to give the title compound as a colorless oil (yield 168 mg, 68%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-864ca784e62745f5acea1da0f3164edc
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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