Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 57026977, compound

HRID 388725Notes

Reaction equation

HRID 388725 reaction equation
[C:1]([O:7][CH2:8][C@@H:9]([C@@H:11]1[C@:19]2([CH3:20])[C@H:14]([C@@H:15]([OH:21])[CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12]1)[CH3:10])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[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.CCOCC>[C:1]([O:7][CH2:8][C@@H:9]([C@@H:11]1[C@:19]2([CH3:20])[C@H:14]([C:15](=[O:21])[CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12]1)[CH3:10])(=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 2724130Cornforth reagent2×HCID 68935884HCID 68935884, compound

Product 1

HCID 57026977HCID 57026977, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The crude compound of Example 3E (0.96 g) was dissolved in 19 mL of dichloromethane and cooled to 0° C.; 3.1 g of pyridinium dichromate was added, followed by 22 mg of pyridinium p-toluenesulfonate. The resultant mixture was stirred for 1.5 hours at 0° C.; an additional 1.3 g of pyridinium dichromate and 20 mg of pyridinium p-toluenesulfonate were added, and the mixture was allowed to warm to ambient temperature overnight. The mixture was diluted with ether and filtered through a pad of diatomaceous earth with an ether wash. The filtrate was washed with 1 N aqueous HCl, and then filtered through a plug of silica gel. The crude product was purified by chromatography on an Analogix IntelliFlash 280™, eluting with a gradient of 8% to 15% ethyl acetate in hexanes. Fractions containing the titled compound were combined and concentrated in vacuo (0.77 g, 96%, 2 steps).

Workup

  1. temperatureto warm to ambient temperature overnight
  2. filtrationfiltered through a pad of diatomaceous earth with an ether
  3. washwash
  4. washThe filtrate was washed with 1 N aqueous HCl
  5. filtrationfiltered through a plug of silica gel
  6. customThe crude product was purified by chromatography on an Analogix IntelliFlash 280™
  7. washeluting with a gradient of 8% to 15% ethyl acetate in hexanes
  8. additionFractions containing the titled compound
  9. concentrationconcentrated in vacuo (0.77 g, 96%, 2 steps)

Sources & evidence

ORD record
ord-ee836d9f30f14d5d82ced9686f9667a3
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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