Water → N-(dimethyloxophosphinyl-methyl)-N-[3-(2-amino-ethoxy)-5-methyl-phenyl]-2-methoxy-benzenesulfonamide

HRID 399736Notes

Reaction equation

HRID 399736 reaction equation
Cl[Si](C)(C)C.[BH4-].[Li+].[CH3:8][C:9]([CH3:36])([P:33](=[O:35])=[O:34])[N:10]([C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([O:29][CH2:30][C:31]#[N:32])[CH:23]=1)[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])(=[O:13])=[O:12].O>O1CCCC1>[CH3:8][C:9]([CH3:36])([P:33](=[O:35])=[O:34])[N:10]([C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([O:29][CH2:30][CH2:31][NH2:32])[CH:23]=1)[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])(=[O:12])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 53934650HCID 53934650, compound

Product 1

HCID 23206743N-(dimethyloxophosphinyl-methyl)-N-[3-(2-amino-ethoxy)-5-methyl-phenyl]-2-methoxy-benzenesulfonamideYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.3 ml Chlorotrimethylsilane was added dropwise under nitrogen and while cooling on ice to 0.29 g (13.2 mmol) lithium borohydride in 5 ml tetrahydrofuran, it was stirred for 1 h at room temperature, a solution of 0.93 g (2.2 mmol) N-(dimethyloxophosphinyl-methyl)-N-(3-cyanomethoxy-5-methyl-phenyl)-2-methoxy-benzenesulfonamide in 5 ml tetrahydrofuran was added dropwise, it was stirred for 1 h at room temperature, water was added dropwise, the solvent was removed in a vacuum, it was taken up in a small amount of dichloromethane and filtered over silica gel (dichloromethane:methanol=9:1), the solvent was removed in a vacuum and 900 mg (91%) N-(dimethyloxophosphinyl-methyl)-N-[3-(2-amino-ethoxy)-5-methyl-phenyl]-2-methoxy-benzenesulfonamide was obtained as an oil. MS (m/e)=426.

Workup

  1. stirringit was stirred for 1 h at room temperature
  2. customthe solvent was removed in a vacuum, it
  3. filtrationfiltered over silica gel (dichloromethane:methanol=9:1)
  4. customthe solvent was removed in a vacuum

Sources & evidence

ORD record
ord-695f59f5ec4448e39ecc5bf3c4049984
Source dataset
uspto-grants-1998_10
Patent number
US05824679

Reaction notes

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