Phosphate → N2-[(3-Iodophenyl)sulfonyl]-N2-{[2-(trimethylsilyl)ethoxy]methyl}glycinamide

HRID 720860Notes

Reaction equation

HRID 720860 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH2:12][C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl.P([O-])([O-])([O-])=O>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]([CH2:23][O:22][CH2:21][CH2:20][Si:19]([CH3:26])([CH3:25])[CH3:18])[CH2:12][C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21895595N2-[(3-Iodophenyl)sulfonyl]glycinamide

Product 1

HCID 69197160N2-[(3-Iodophenyl)sulfonyl]-N2-{[2-(trimethylsilyl)ethoxy]methyl}glycinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N2-[(3-Iodophenyl)sulfonyl]glycinamide (0.14 g) was stirred with sodium hydride (60% oil dispersion, 0.02 g) in DMF (2 ml) at 21° under nitrogen for 15 min. 2-Trimethylsilylethoxymethyl chloride (0.08 ml) was added and stirring was continued for 1.5 h. The mixture was poured into pH 6.4 phosphate buffer and the product was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), concentrated and applied to a silica Bond Elut Cartridge (5 g) in dichloromethane containing methanol. The cartridge was eluted with dichloromethane, diethyl ether and ethyl acetate to give the title compound (0.16 g), LCMS RT=3.49 min.

Workup

  1. extractionthe product was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additioncontaining methanol
  6. washThe cartridge was eluted with dichloromethane, diethyl ether and ethyl acetate

Sources & evidence

ORD record
ord-ef7c65d78b3947db9f99f48f3578805d
Source dataset
uspto-grants-2006_11
Patent number
US07135600B2

Reaction notes

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