methyl (S)-3-(4-benzyloxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate → methyl (S)-3-(4-hydroxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate

HRID 2202178Notes

Reaction equation

HRID 2202178 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH2:19][C@H:20]([N:25]2[CH2:30][CH2:29][N:28]([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:27][CH2:26]2)[C:21]([O:23][CH3:24])=[O:22])(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.O1CCOCC1.C(O)(=O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH2:19][C@H:20]([N:25]2[CH2:26][CH2:27][N:28]([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:29][CH2:30]2)[C:21]([O:23][CH3:24])=[O:22])(=[O:16])=[O:17])=[CH:11][CH:10]=1

Participants

6

Reactant 1

HCID 86675014methyl (S)-3-(4-benzyloxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate

Product 1

HCID 86675015methyl (S)-3-(4-hydroxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoateYield 100.4%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2.0 g (3.9 mmol) of methyl (S)-3-(4-benzyloxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate (prepared as described in example 3.6) in 60 ml of ethanol, 30 ml of dioxane and 0.5 ml of glacial acetic acid is degassed under a nitrogen stream and then 200 mg (10% by weight) of palladium-on-carbon at 10% in suspension in 3 ml of dioxane are added. The reaction medium is placed under a hydrogen atmosphere and stirred at ambient temperature for 18 h. After filtration through celite, the filtrate is hydrolyzed and then the product is extracted with ethyl acetate. The organic phase is washed with water and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. 1.65 g (100%) of methyl (S)-3-(4-hydroxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate are obtained in the form of a white solid.

Workup

  1. filtrationAfter filtration through celite
  2. extractionthe product is extracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-415d24429a6c42a694f2fa6625b8eb03
Source dataset
uspto-grants-2016_06
Patent number
US09365529B2

Reaction notes

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