HCID 22476579, compound → HCID 10267727, compound

HRID 2184412Notes

Reaction equation

HRID 2184412 reaction equation
[OH:1][C:2]1([C:15]2[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[CH:17][CH:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10]>[Pd].C(OCC)(=O)C>[OH:1][C:2]1([C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10]

Participants

4

Reactant 1

HCID 22476579HCID 22476579, compound

Product 1

HCID 10267727HCID 10267727, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

{2-Hydroxy-2-[4-(phenylmethoxy)phenyl]cyclohexyl}[(methylethyl)sulfonyl]amine (5.00 g, 12.8 mmol) was combined with 5% palladium on carbon in ethyl acetate (200 mL) mixed together and placed on the power shaker under a hydrogen atmosphere at 45 psl's overnight. The solution was filtered over a Celite® mat and the resulting filtrate was concentrated under reduced vacuum to yield 4.1 g as a white solid. This material was purified via silica gel chromatography employing the Water's prep. 2000 while eluting with a solvent of methylene chloride/methanol 9:1 to provide the title compound (3.75 g 94%) as a white solid. Ion Spray M.S. 312.1 (M*−1). Calculated for C15H23NO4S: Theory: C 57.48, H 7.40, N 4.47. Found: C 57.11, H 7.40, N 4.65.

Workup

  1. additionmixed together
  2. customplaced on the power shaker under a hydrogen atmosphere at 45 psl's overnight
  3. filtrationThe solution was filtered over a Celite® mat
  4. concentrationthe resulting filtrate was concentrated under reduced vacuum
  5. customto yield 4.1 g as a white solid
  6. customThis material was purified via silica gel chromatography
  7. wash2000 while eluting with a solvent of methylene chloride/methanol 9:1

Sources & evidence

ORD record
ord-dd3bf7c7a28c4f6ebe87d6d7a202ea0c
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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