Acetone → HCID 68291841, compound

HRID 339919Notes

Reaction equation

HRID 339919 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH2:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])(=[O:9])=[O:8].C([Li])CCC.[CH3:31][C:32]([CH3:34])=[O:33].FC(F)(F)C(O)=O>C1COCC1>[OH:33][C:32]([CH3:34])([CH3:31])[CH:10]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])[S:7](=[O:8])(=[O:9])[NH2:6]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 68291922HCID 68291922, compoundHCID 178418339Butyllithium

Product 1

HCID 68291841HCID 68291841, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[(2,4-dimethoxybenzylsulfamoyl)methyl]benzoic acid (4.1 g) in THF (50 ml) was added dropwise, at −78° C., butyllithium (1.6 M, 25 ml). The mixture was stirred for 10 min. Subsequently, acetone (4.5 ml) was added and the mixture was stirred at −78° C. for a further 30 min. The reaction mixture was then admixed with trifluoroacetic acid (4 ml) and concentrated. The residue was suspended in dichloromethane and trifluoroacetic acid (10 ml) admixed. After 2 h, water was added and the mixture was filtered. The aqueous phase was removed and freeze-dried. The residue was purified by means of preparative HPLC. This gave the product (1.1 g) with a molecular weight of 273.3 g/mol (C11H15NO5S).

Workup

  1. stirringthe mixture was stirred at −78° C. for a further 30 min
  2. concentrationconcentrated
  3. waitAfter 2 h
  4. additionwater was added
  5. filtrationthe mixture was filtered
  6. customThe aqueous phase was removed
  7. customfreeze-dried
  8. customThe residue was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-ab737a609bb04c75b8cf3afc10ffb5e3
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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