4-Toluenesulfonyl chloride → HCID 86628507, compound

HRID 546681Notes

Reaction equation

HRID 546681 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH:31]([CH3:35])[CH2:32][CH2:33][OH:34])[C:20]([NH:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21])=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:34][CH2:33][CH2:32][CH:31]([CH3:35])[CH:19]([C:16]2[CH:15]=[CH:14][C:13]([F:12])=[CH:18][CH:17]=2)[C:20]([NH:22][NH:23][C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[O:21])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 66839506HCID 66839506, compound

Product 1

HCID 86628507HCID 86628507, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Toluenesulfonyl chloride (321 mg) was added to a solution of tert-butyl N′-[2-(4-fluorophenyl)-5-hydroxy-3-methylpentanoyl]hydrazinecarboxylate (520 mg) in pyridine (6 mL). The reaction solution was stirred at room temperature for 12 hours and then concentrated under reduced pressure. Ethyl acetate and brine were added to the residue, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 335 mg of the title compound. The property value of the compound is as follows.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate and brine were added to the residue
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-1cc22feaa8e74c35885baf36cbfd27c4
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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