4-Chlorobenzenesulfonyl chloride → HCID 54757662, compound

HRID 41143Notes

Reaction equation

HRID 41143 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[CH2:9][CH:10]1[C:14](=[O:15])[CH:13]=[C:12]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:11]1)=[N+]=[N-].[H][H].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>CO.C(OCC)(=O)C.[Pd]>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:1][CH2:4][CH2:5][C:6]2[CH:23]=[CH:22][CH:21]=[C:8]([CH2:9][CH:10]3[CH2:11][C:12]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:13][C:14]3=[O:15])[CH:7]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

7

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 547576615-(3-(2-Azidoethyl)benzyl)-3-isobutoxycyclopent-2-enoneHCID 178418361HCID 178418361, compound

Product 1

HCID 54757662HCID 54757662, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 31 (0.059 g, 0.19 mmol) and Pd on C (10 wt %, 0.006 g) in methanol (3 mL) is stirred at rt for 1 h under 1 atmosphere of hydrogen. The reaction mixture was filtered to remove the catalyst. Water (0.5 mL) and 2 N sodium hydroxide (0.27 mL) were added and the reaction mixture was cooled to 0° C. in an ice-water bath. Then 4-chlorophenylsulfonyl chloride (0.082 g, 0.39 mmol) was added and the reaction mixture was stirred at 0° C. for 4 h and then diluted with ethyl acetate. The organic layer was collected, washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue so obtained was purified by silica gel column chromatography, using ethyl acetate-hexanes 1:1 as eluent, to provide the desired compound. Yield: 22%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. additionWater (0.5 mL) and 2 N sodium hydroxide (0.27 mL) were added
  4. customThe organic layer was collected
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue so obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-20ab230593154130aeca0b687c631723
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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