Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68938899, compound

HRID 388735Notes

Reaction equation

HRID 388735 reaction equation
[CH3:1][O:2][CH:3]([CH2:17][C@@H:18]([CH3:24])[C:19]([O:22][CH3:23])([CH3:21])[CH3:20])[C@H:4]([C@@H:6]1[C@:14]2([CH3:15])[C@H:9]([C@@H:10]([OH:16])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)[CH3:5].[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>[CH3:1][O:2][CH:3]([CH2:17][C@@H:18]([CH3:24])[C:19]([O:22][CH3:23])([CH3:21])[CH3:20])[C@H:4]([C@@H:6]1[C@:14]2([CH3:15])[C@H:9]([C:10](=[O:16])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)[CH3:5]

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 2724130Cornforth reagentHCID 68673533HCID 68673533, compound

Product 1

HCID 68938899HCID 68938899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 10H (27 mg, 0.079 mmol) was dissolved in 1 mL of dichloromethane; 150 mg of pyridinium dichromate and 10 mg of pyridinium p-toluenesulfonate were added, and the resultant mixture was stirred overnight at ambient temperature. Diatomaceous earth (˜500 mg) was added, and the solvents were removed in vacuo. The residue was taken up in ethyl acetate and loaded onto a plug of silica. Elution with a gradient of 50% to 100% ethyl acetate in hexanes, and concentration of the combined eluate, gave a product which was carried forward without further purification.

Workup

  1. additionDiatomaceous earth (˜500 mg) was added
  2. customthe solvents were removed in vacuo
  3. washElution with a gradient of 50% to 100% ethyl acetate in hexanes, and concentration of the combined eluate
  4. customgave a product which
  5. customwas carried forward without further purification

Sources & evidence

ORD record
ord-b9dc6911f35543e2929a2406e1c58eb7
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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