Hydrochloric Acid → HCID 22137342, compound

HRID 1827589Notes

Reaction equation

HRID 1827589 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29]C3CCCCO3)=[CH:25][CH:24]=2)[S:10]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])(=[O:12])=[O:11])=[CH:5][CH:4]=1.Cl>C(O)C>[OH:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[S:10]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])(=[O:12])=[O:11])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22137380HCID 22137380, compound

Product 1

HCID 22137342HCID 22137342, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude N-(4-methoxy-phenyl)-2,4,6-trimethyl-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide prepared in Step A was suspended in 2 mL of a 3:1 (v/v) mixture of ethanol:1N HCl and was stirred at room temperature overnight. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and the aqueous solution was washed with methylene chloride. The organic layer was concentrated. The residue was purified by reverse phase HPLC (98:2 water:0.1% trifluoracetic acid to 98:2 acetonitrile:water) to afford the title compound. MS 411 (M+1)+

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. washthe aqueous solution was washed with methylene chloride
  3. concentrationThe organic layer was concentrated
  4. customThe residue was purified by reverse phase HPLC (98:2 water:0.1% trifluoracetic acid to 98:2 acetonitrile:water)

Sources & evidence

ORD record
ord-86864bdd6fd8407bb7f465af17d30c4f
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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