Hydrogen Peroxide → tert-Butyl-4-({[4-(2-butynyloxy)phenyl]sulfinyl}methyl)-4-[(hydroxyamino)carbonyl]-1-piperidinecarboxylate

HRID 353555Notes

Reaction equation

HRID 353555 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][S:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=2)([C:14]([NH:16][OH:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:31]O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][S:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=2)=[O:31])([C:14]([NH:16][OH:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 23513813Tert-butyl-4-({[4-(2-butynyloxy)phenyl]sulfanyl)methyl)-4-[(hydroxyamino)carbonyl]-1-piperidinecarboxylate

Product 1

HCID 23513828tert-Butyl-4-({[4-(2-butynyloxy)phenyl]sulfinyl}methyl)-4-[(hydroxyamino)carbonyl]-1-piperidinecarboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slurry of tert-butyl-4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-4-[(hydroxyamino) carbonyl]-1-piperidinecarboxylate (0.24 g, 0.55 mmol) at 0° C. in 7 mL of MeOH was added dropwise 3.5 mL of 30% hydrogen peroxide. The reaction was allowed to warm to room temperature and stirred for 18 h. The reaction was cooled to 0° C. and quenched with 3.5 mL of a saturated solution of Na2SO3. The organaics were removed and the aqueous solution was extracted with CH2Cl2. The organics were washed with H2O, brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether to provide 0.166 g (67%) of the desired product as an off white solid. Electrospray Mass Spec: 451.3 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with 3.5 mL of a saturated solution of Na2SO3
  3. customThe organaics were removed
  4. extractionthe aqueous solution was extracted with CH2Cl2
  5. washThe organics were washed with H2O, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-f9ec373b40784bd0a92d8e98a477e78c
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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