Benzenesulfonyl chloride → HCID 18449978, compound

HRID 2100440Notes

Reaction equation

HRID 2100440 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH3:2].C([Li])CCC.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[C:22]1([S:28]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([CH2:1][CH3:2])=[CH:11][CH:10]=3)[C:6]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:7]2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 17984209HCID 17984209, compoundHCID 178418339Butyllithium

Product 1

HCID 18449978HCID 18449978, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The indole propionic acid 14 (100 mg, 0.46 mmol) was dissolved in THF (5.0 mL) and cooled to −78° C. To this solution was added n-butyllithium (n-BuLi; 0.4 mL, 1.0 mmol, 2.4 M in hexanes) dropwise and the mixture was stirred at −78° C. for 1 hour. To this mixture was added benzenesulfonyl chloride (0.13 mL, 1 mmol) and the reaction was allowed to stir overnight and warm to room temperature. The mixture was poured into ice cold H3PO4 and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography (5% MeOH/CHCl3) to give compound 6 as a white solid (10 mg; M−1=356.4).

Workup

  1. stirringto stir overnight
  2. temperaturewarm to room temperature
  3. additionThe mixture was poured into ice cold H3PO4
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-b45f7bc4602647afb737ef7b994b20b5
Source dataset
uspto-grants-2009_08
Patent number
US07572806B2

Reaction notes

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