Hydrochloric Acid → N-hydroxy-4-(2'-hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide

HRID 533544Notes

Reaction equation

HRID 533544 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([CH3:31])([S:27]([CH3:30])(=[O:29])=[O:28])[C:17]([NH:19][O:20]C2CCCCO2)=[O:18])=[CH:10][CH:9]=1.Cl.CO>C(Cl)Cl>[OH:20][NH:19][C:17](=[O:18])[C:16]([CH3:31])([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:15][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[OH:1])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86668768HCID 86668768, compound

Product 1

HCID 86668769N-hydroxy-4-(2'-hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2′-Hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (19.6 mg, 0.044 mmol) was dissolved in methylene chloride (1 mL) at ambient temperature. To this solution was added HCl (4M in 1,4-dioxane, 0.33 mL, 1.32 mmol) and the solution was stirred at RT for 5 minutes. Methanol (100 uL) was added followed by silica gel and the mixture was concentrated to dryness. The crude material was purified via silica gel chromatography and eluted with methylene chloride/methanol to afford N-hydroxy-4-(2′-hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide as a solid. 6.5 mg

Workup

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

Sources & evidence

ORD record
ord-36041b3f45ca4fb8a56b6dc6576eca90
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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