Hydrochloric Acid → 4-(4-cyclohept-1-en-1-ylphenyl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 533559Notes

Reaction equation

HRID 533559 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([CH3:32])([S:28]([CH3:31])(=[O:30])=[O:29])[C:17]([NH:19][O:20]C(OC)CCCC)=[O:18])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.Cl.CO>C(Cl)Cl>[C:1]1([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([CH3:32])([S:28]([CH3:31])(=[O:30])=[O:29])[C:17]([NH:19][OH:20])=[O:18])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 866687754-(4-cyclohept-1-en-1-ylphenyl)-N-[(1-methoxypentyl)oxy]-2-methyl-2-(methylsulfonyl)butanamide

Product 1

HCID 866687764-(4-cyclohept-1-en-1-ylphenyl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Cyclohept-1-en-1-ylphenyl)-N-[(1-methoxypentyl)oxy]-2-methyl-2-(methylsulfonyl)butanamide (205 mg, 0.36 mmol) was dissolved in methylene chloride (4 mL) at ambient temperature. To this solution was added HCl (4M in 1,4-dioxane, 1.82 mL, 7.30 mmol) and the solution was stirred at rt for 20 minutes. Methanol (500 uL) was added followed by silica gel and the mixture was concentrated to dryness. The crude material was purified via silica gel chromatography eluting with methylene chloride/methanol to afford 4-(4-cyclohept-1-en-1-ylphenyl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide as a solid. 91.5 mg. LCMS: (M+1) 366.2.

Workup

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

Sources & evidence

ORD record
ord-02d9f4ba1eeb4c128dace1dea60fb6cc
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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