p-Toluenesulfonic acid monohydrate → HCID 86622729, compound

HRID 2410336Notes

Reaction equation

HRID 2410336 reaction equation
[CH2:1]([O:5][C:6]1[C:11]2[C:12]([O:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]4([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH2:19][CH2:18]3)=[N:13][O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH:2]([CH3:4])[CH3:3].O.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([OH:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(OCC)(=O)C>[C:32]1([CH3:42])[CH:33]=[CH:34][C:35]([S:38]([O-:41])(=[O:39])=[O:40])=[CH:36][CH:37]=1.[OH:30][C:24]1([CH2:23][NH+:20]2[CH2:19][CH2:18][CH:17]([CH2:16][O:15][C:12]3[C:11]4[C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:7][CH:8]=[CH:9][C:10]=4[O:14][N:13]=3)[CH2:22][CH2:21]2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53357029HCID 53357029, compound

Product 1

HCID 86622729HCID 86622729, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

4-[(4-{[(4-Isobutoxy-1,2-benzisoxazol-3-yl)oxy]methyl}piperidin-1-yl)methyl]tetrahydro-2H-pyran-4-ol (34.0 mg, 0.0812 mmol, EXAMPLE 8, step 5) was dissolved in ethyl acetate (approximately 0.3 mL). To this solution was added a solution of p-toluenesulfonic acid monohydrate (21.7 mg, 0.11 mmol) in ethyl acetate (2 mL) at room temperature. After being stirred for 30 min, resulting white precipitate was filtered and washed with ethyl acetate to afford 45 mg (93%) of the title compound as a white powdery solid.

Workup

  1. customresulting white precipitate
  2. filtrationwas filtered
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-22aa799c05aa48e9b497ebc85754c44b
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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