4-Toluenesulfonyl chloride → HCID 86628509, compound

HRID 546689Notes

Reaction equation

HRID 546689 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.[OH:12][CH:13]([CH2:36][OH:37])[CH2:14][CH:15]([C:27]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[C:29]([F:35])[CH:28]=1)[C:16]([NH:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:37][CH2:36][CH:13]([OH:12])[CH2:14][CH:15]([C:27]2[CH:32]=[C:31]([F:33])[C:30]([F:34])=[C:29]([F:35])[CH:28]=2)[C:16]([NH:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 66839410HCID 66839410, compound

Product 1

HCID 86628509HCID 86628509, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Toluenesulfonyl chloride (605 mg) was added to a solution of tert-butyl N′-[4,5-dihydroxy-2-(3,4,5-trifluorophenyl)pentanoyl]hydrazinecarboxylate (1.09 g) in pyridine (11 mL) at room temperature. The reaction solution was stirred at room temperature for 12 hours and then concentrated under reduced pressure. Ethyl acetate was added to the residue, and the organic layer was washed with brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 1.03 g of the title compound. The property value of the compound is as follows.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium 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-ba5507f66a944a94ba73f3ecce420e5b
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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