Acetic Acid → HCID 58941462, compound

HRID 747619Notes

Reaction equation

HRID 747619 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:22][CH2:23][O:24]C2CCCCO2)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([CH:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])[OH:32])[CH:3]=1.C(O)(=O)C.O>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:22][CH2:23][OH:24])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([CH:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])[OH:32])[CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 68567822HCID 68567822, compound

Product 1

HCID 58941462HCID 58941462, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To 0.479 g of N-{4-chloro-2-[(2-chlorophenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxy-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzenesulfonamide dissolved in 4.7 ml of THF are added 9.15 ml of acetic acid and 2.25 ml of water, and the mixture is maintained at 40° C. for 48 hours. The reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a cyclohexane/ethyl acetate solvent mixture to give 0.209 g of the expected product.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on a column of silica gel
  5. washeluting with a cyclohexane/ethyl acetate solvent mixture

Sources & evidence

ORD record
ord-f0bf1f29fcc74386935275cdef59ea13
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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