3-Benzyloxy-1-(toluene-4-sulfonylmethyl)-1H-pyridin-2-one → 3-Hydroxy-1-(toluene-4-sulfonylmethyl)-1h-pyridin-2-one

HRID 1716306Notes

Reaction equation

HRID 1716306 reaction equation
C([O:8][C:9]1[C:10](=[O:26])[N:11]([CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CS(O)(=O)=O>[OH:8][C:9]1[C:10](=[O:26])[N:11]([CH2:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 685103983-Benzyloxy-1-(toluene-4-sulfonylmethyl)-1H-pyridin-2-one

Product 1

HCID 444558373-Hydroxy-1-(toluene-4-sulfonylmethyl)-1h-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 3-benzyloxy-1-(toluene-4-sulfonylmethyl)-1H-pyridin-2-one (50 mg) from Step B in MeSO3H (1.5 mL) was stirred at room temperature for 20 min and then quenched with ice water. The solid was filtered off and washed with water. The crude product was re-dissolved in hot MeOH (1 mL) and removed un-dissolved brownish solid. The filtrate was concentrated in vacuo to give the titled compound. MS (EI) 280 (M+H)+.

Workup

  1. customquenched with ice water
  2. filtrationThe solid was filtered off
  3. washwashed with water
  4. dissolutionThe crude product was re-dissolved in hot MeOH (1 mL)
  5. customremoved
  6. dissolutionun-dissolved brownish solid
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-769f85478d454fe49c95ee592e78da34
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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