4-Toluenesulfonyl chloride → HCID 14697189, compound

HRID 846333Notes

Reaction equation

HRID 846333 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH:9][CH:10]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13])[C:3]=1[O:20][CH2:21][CH:22]([OH:24])[CH3:23].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(OCC)(=O)C>N1C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:16]([O:18][CH3:19])=[O:17])[C:3]=1[O:20][CH2:21][CH:22]([O:24][S:31]([C:28]1[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=1)(=[O:33])=[O:32])[CH3:23]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 14697187HCID 14697187, compound

Product 1

HCID 14697189HCID 14697189, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2.07 g of the compound obtained in Example 6 in 4.2 ml of pyridine was added 1.49 g of p-toluenesulfonyl chloride and the mixture was stirred at an external temperature of 5° C. for 3 days. To the mixture was added ethyl acetate, and the solution was washed successively with 1 N hydrochloric acid, a saturated sodium bicarbonate aqueous solution and water, and then dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography to yield 2.76 g of the titled compound.

Workup

  1. washthe solution was washed successively with 1 N hydrochloric acid
  2. dry with materiala saturated sodium bicarbonate aqueous solution and water, and then dried over anhydrous magnesium sulfate The solvent
  3. customwas removed under reduced pressure
  4. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-1884dece45734fde8bba8c376be86542
Source dataset
uspto-grants-1992_08
Patent number
US05136059

Reaction notes

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