Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 25068477, compound

HRID 388730Notes

Reaction equation

HRID 388730 reaction equation
[OH:1][C:2]([CH3:20])([CH3:19])[CH2:3][CH2:4][O:5][C@H:6]([C@@H:8]1[C@:16]2([CH3:17])[C@H:11]([C@@H:12]([OH:18])[CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9]1)[CH3:7].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[OH:1][C:2]([CH3:19])([CH3:20])[CH2:3][CH2:4][O:5][C@H:6]([C@@H:8]1[C@:16]2([CH3:17])[C@H:11]([C:12](=[O:18])[CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9]1)[CH3:7]

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 2724130Cornforth reagentHCID 15816085HCID 15816085, compound

Product 1

HCID 25068477HCID 25068477, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 8F (70 mg, 0.25 mmol) was dissolved in 1.5 mL of dichloromethane; 350 mg of pyridinium dichromate and 15 mg of pyridinium p-toluenesulfonate were added, and the resultant mixture was stirred overnight at ambient temperature. Solvents were removed in vacuo; the residue was taken up in ethyl acetate and filtered through diatomaceous earth washing with ethyl acetate. The filtrate was concentrated and the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient of 10% to 40% ethyl acetate in hexanes, to isolate the titled compound (65 mg, 73%).

Workup

  1. customSolvents were removed in vacuo
  2. filtrationfiltered through diatomaceous earth
  3. washwashing with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography on an Analogix Intelliflash 280™
  6. washeluting with a gradient of 10% to 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b44c0c159f7d493199e17d638c75b712
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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