Isobutyl iodide → HCID 69412898, compound

HRID 1592752Notes

Reaction equation

HRID 1592752 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH2:27](I)[CH:28]([CH3:30])[CH3:29]>CN(C=O)C>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]([CH2:27][CH:28]([CH3:30])[CH3:29])[S:21]([CH3:24])(=[O:23])=[O:22])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 21935212Tert-Butyl 4-(2-[(Methylsulfonyl)Amino]Phenyl)-Piperazinecarboxylate

Product 1

HCID 69412898HCID 69412898, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-boc-4-(2-methanesulfonylamino-phenyl)-piperazine (1.07 g, 3.0 mmol) in 50 mL of DMF was added NaH (240 mg of a 60% dispersion in oil, 6 mmol). After stirring for about 15 minutes at r.t., isobutyl iodide (420 □L, 3.65 mmol) was added and the solution warmed to 60° C. After stirring at 60° C. overnight, the reaction was quenched with saturated aqueous ammonium chloride and diluted with EtOAc. The solution was washed twice with water and brine, and then dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (40M Biotage column, 10-30% linear gradient EtOAc/Hex, over 45 min at 35 mL/min) afforded about 1.07 g (2.6 mmol, 87%) of the title compound as a white foam. LRMS: 412.3 (M+1)

Workup

  1. temperaturethe solution warmed to 60° C
  2. stirringAfter stirring at 60° C. overnight
  3. customthe reaction was quenched with saturated aqueous ammonium chloride
  4. additiondiluted with EtOAc
  5. washThe solution was washed twice with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (40M Biotage column, 10-30% linear gradient EtOAc/Hex, over 45 min at 35 mL/min)

Sources & evidence

ORD record
ord-b7787f96a7c245d7a4e94073703f78c1
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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