Sodium Bicarbonate → HCID 23378640, compound

HRID 1279620Notes

Reaction equation

HRID 1279620 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:12](=[O:14])[CH3:13])=[C:7]([O:24][CH3:25])[CH:6]=1)(O)[CH3:3].C(=O)([O-])O.[Na+]>C(Cl)Cl.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[CH3:25][O:24][C:7]1[CH:6]=[C:5]([CH:2]([CH3:1])[CH3:3])[CH:10]=[CH:9][C:8]=1[N:11]([S:15]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:16])=[O:17])[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 22672035HCID 22672035, compound

Product 1

HCID 23378640HCID 23378640, compoundYield 97.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Procedure

To a solution of 1-methyl-1-[4-(N-acetyl-phenylsulfonylamino)-3-methoxyphenyl]ethanol (2.50 g; prepared in Reference Example 39.) in methylene chloride (10 ml), trifluoroacetic acid (10 ml) and triethylsilane (3.3 ml) were added at 0° C. The mixture was stirred for 1 hour at room temperature. The reaction mixture was added to saturated sodium hydrogencarbonate carefully The mixture was extracted with ethyl acetate. The organic layer was washed, dried over and concentrated. The residue was purified on silica gel column chromatography (hexane:AcOEt=3:1) to give the title compound (2.33 g) having the following physical data.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried over and
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel column chromatography (hexane:AcOEt=3:1)

Sources & evidence

ORD record
ord-2c798ae8521f460db39718215a73b381
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

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