HCID 22176567, compound → HCID 22176564, compound

HRID 1797193Notes

Reaction equation

HRID 1797193 reaction equation
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:2]([OH:1])([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:9])[CH3:10])(=[O:7])=[O:6])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 22176567HCID 22176567, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22176564HCID 22176564, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

900 mg of [2-hydroxy-2-(4-nitrophenyl)propyl][(methylethyl)sulfonyl]amine and 1.2 equivalence of 10% Pd/C in ethyl acetate (50 mL) were subjected to a hydrogen atmosphere while shaking at 60 psi for 3 hours. Solution was filtered through a Celite® mat and the resulting filtrate was concentrated under reduced vacuum to yield 720 mg as an oil. This material was purified via silica gel chromatography employing the Chromatotron and using a 4000 micron rotor while eluting with a solvent of hexane/ethyl acetate 1:1 to yield the intermediate title compound (340 mg, 42%) as a tan solid. Ion spray M.S. 271.4 (M*−1).

Workup

  1. filtrationSolution was filtered through a Celite® mat
  2. concentrationthe resulting filtrate was concentrated under reduced vacuum
  3. customto yield 720 mg as an oil
  4. customThis material was purified via silica gel chromatography
  5. washwhile eluting with a solvent of hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-1f39119d00e942d5b93415f20f62844e
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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