Phosphate → 3-(Hydroxymethyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

HRID 916814Notes

Reaction equation

HRID 916814 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1.[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl.P([O-])([O-])([O-])=O>CN(C=O)C.C(OCC)(=O)C>[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([S:11]([N:14]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])(=[O:12])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 231337993-(Hydroxymethyl)benzene-1-sulfonamide

Product 1

HCID 468348293-(Hydroxymethyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oil dispersion, 0.315 g) was added to 3-hydroxymethylbenzenesulfonamide (0.67 g) with stirring in DMF (20 ml) under nitrogen at 20°. After 15 min, 2-(trimethylsilyl)ethoxymethyl chloride (1.27 ml) was added and stirring was continued for 1.5 h. pH 6.4 Phosphate buffer and ethyl acetate were added. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were washed twice with brine, dried (MgSO4) and evaporated to an oil. This oil in dichloromethane was loaded onto a column of silica gel (75 g) set up in 10% ethyl acetate in 40-60 petroleum ether. The column was run with this, then 20%, 30% and 50% ethyl acetate in 40-60 petroleum ether to give the title compound (0.74 g) LCMS RT=4.00 min.

Workup

  1. waitwas continued for 1.5 h.
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washthe combined organic layers were washed twice with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to an oil

Sources & evidence

ORD record
ord-e5dcef96f04b491296cc3d16eb085358
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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