p-Toluenesulfonic acid monohydrate → HCID 19085846, compound

HRID 962736Notes

Reaction equation

HRID 962736 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[S:13]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[S:13]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19085864HCID 19085864, compound

Product 1

HCID 19085846HCID 19085846, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1 g of 2-(4-(2-tetrahydropyranyloxy)butyl)-isothiazolo[5,4-c]pyridin-3(2H)-one and 0.1 g of p-toluenesulfonic acid monohydrate in 50 mL of methanol was stirred overnight at ambient temperature and concentrated to dryness under reduced pressure. The residue was dissolved in 200 mL of ethyl acetate, washed with 4 mL of saturated sodium bicarbonate, dried over MgSO4 and concentrated under reduced pressure. Drying under vacuum overnight gave 0.73 g (78%) of 2-(4-hydroxybutyl)-isothiazolo[5,4-c]pyridin-3(2H)-one as an oil: 1H NMR (400 MHz, CDCl3): 9.28 (s, 1H), 9.15 (d, J=5 Hz, 1H), 7.98 (d, J=5Hz, 1H), 3.86 (t, J=7.5 Hz, 2H), 3.71 (t, J=6.4 Hz, 2H), 2.36 (br s, 1H), 1.98 (m, 2H), 1.27 (m, 2H).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in 200 mL of ethyl acetate
  3. washwashed with 4 mL of saturated sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customDrying under vacuum overnight

Sources & evidence

ORD record
ord-f00bee81720149e1b7ed48be60fbdf40
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

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