HCID 22476602, compound → HCID 22476611, compound

HRID 2184410Notes

Reaction equation

HRID 2184410 reaction equation
[OH:1][CH:2]1[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].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:14][CH:12]([S:9]([NH:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1=[O:1])(=[O:11])=[O:10])[CH3:13]

Participants

4

Reactant 2

HCID 22476602HCID 22476602, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22476611HCID 22476611, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 500 mL single neck flask (2-hydroxycyclohexy)[(methylethyl)sulfonyl]amine (6.78 g, 30.6 mmol) was combined with pyridinium chlorochromate (7.92 g, 1.2 eq) in methylene chloride (300 mL) and stirred at room temperature under a nitrogen atmosphere for 4 hours. The solution was then filtered over a Celite® mat and the organic layer was washed once with water, dried over potassium carbonate, filtered, and concentrated under reduced vacuum to yield 13.42 g as a dark oil. This material was purified via silica gel chromatography employing the Water's Prep. 2000 and eluting with a solvent of methylene chloride/ethyl acetate 19:1 to yield the intermediate title compound (3.95 g, 59%). as a white solid. Ion Spray M.S. 218 (M*−1). Calculated for C9H17NO3S: Theory: C 49.29, H 7.81, N 6.39. Found: C 49.25, H 7.58, N 6.32.

Workup

  1. filtrationThe solution was then filtered over a Celite® mat
  2. washthe organic layer was washed once with water
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced vacuum
  6. customto yield 13.42 g as a dark oil
  7. customThis material was purified via silica gel chromatography
  8. wash2000 and eluting with a solvent of methylene chloride/ethyl acetate 19:1

Sources & evidence

ORD record
ord-776bc7e5e0d54706bc47ae0b165067ed
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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