Iodoethane → HCID 58786706, compound

HRID 1376042Notes

Reaction equation

HRID 1376042 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[CH2:15][NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:31][CH3:32]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[CH2:15][N:16]([CH2:31][CH3:32])[S:17]([CH3:20])(=[O:19])=[O:18])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 58786412HCID 58786412, compound

Product 1

HCID 58786706HCID 58786706, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-[1-(2-Fluoro-phenyl)-2-methanesulfonylamino-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (408) (1.43 g, 3.56 mmol) in THF (30 mL) was added NaH (60% in oil) (0.16 g, 3.92 mmol) and the solution was allowed to stir for 1 h at room temperature. Iodoethane (0.31 mL, 3.92 mmol) was then added and the reaction was allowed to stir for 18 h. The reaction mixture was diluted with EtOAc (100 mL) and washed with H2O (100 mL). The organic phase was concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 10% MeOH in CHCl3) yielding 0.54 g (36%) pure product.

Workup

  1. stirringto stir for 18 h
  2. washwashed with H2O (100 mL)
  3. concentrationThe organic phase was concentrated to dryness
  4. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 10% MeOH in CHCl3)

Sources & evidence

ORD record
ord-ab3e10593fe649578cdf98f1468719ae
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

Loading…