Iodoethane → HCID 18436784, compound

HRID 456473Notes

Reaction equation

HRID 456473 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[O:20][CH2:21][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])([CH3:24])[CH3:23])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH2:32](I)[CH3:33]>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[O:20][CH2:21][C:22]([N:25]([CH2:32][CH3:33])[S:26]([CH3:29])(=[O:28])=[O:27])([CH3:23])[CH3:24])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 18436785HCID 18436785, compound

Product 1

HCID 18436784HCID 18436784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-boc-4-[2-(2-methanesulfonylamino-2-methyl-propoxy)-phenyl]-piperazine (197 mg, 0.46 mmol) in 4 mL of DMF was added NaH (55 mg of a 60% dispersion in oil, 1.38 mmol). After stirring for about 30 minutes, EtI (550 uL, 6.88 mmol) was added. After stirring at 45° C. for about an hour, the mixture was quenched with saturated aqueous sodium bicarbonate. The mixture was diluted with EtOAc, washed with water and brine, and then dried (Na2SO4), filtered and concentrated. The material was combined with 0.36 mmol of crude material from a previous reaction and purified by silica gel chromatography (35 g SiO2, 10 to 30% EtOAc/hexanes, over 30 minutes at 35 mL/min.) to afford about 323 mg (0.71 mmol, 86% combined yield) of the final compound. LRMS (electrospray): 456.2 [M+1]

Workup

  1. stirringAfter stirring at 45° C. for about an hour
  2. customthe mixture was quenched with saturated aqueous sodium bicarbonate
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (35 g SiO2, 10 to 30% EtOAc/hexanes, over 30 minutes at 35 mL/min.)
  9. customto afford

Sources & evidence

ORD record
ord-1d2060bdf3d84a7fa8c7836bcdef158c
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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