Hydrochloric Acid → HCID 76511213, compound

HRID 84279Notes

Reaction equation

HRID 84279 reaction equation
[CH3:1][C:2]([S:29]([CH3:32])(=[O:31])=[O:30])([CH2:13][CH2:14][N:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:17]([CH3:27])[C:16]1=[O:28])[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl.CO>C(Cl)Cl>[OH:6][NH:5][C:3](=[O:4])[C:2]([CH3:1])([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:13][CH2:14][N:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:17]([CH3:27])[C:16]1=[O:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 866719522-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 76511213HCID 76511213, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (137 mg, 0.296 mmol) was dissolved in methylene chloride (2 mL) at ambient temperature. To this solution was added HCl (4M in 1,4-dioxane, 2.22 mL, 8.88 mmol) and the slurry was stirred at ambient temperature for 15 minutes. Methanol (1 mL) was added followed by silica gel and the mixture was concentrated to dryness. Crude material was purified via silica gel chromatography eluting with methylene chloride/methanol to afford N-hydroxy-2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanamide as a solid. 65.8 mg

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. customCrude material was purified via silica gel chromatography
  3. washeluting with methylene chloride/methanol

Sources & evidence

ORD record
ord-a0e3d27c7f8749a6bf8118803cae39eb
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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