4-Toluenesulfonyl chloride → HCID 86667512, compound

HRID 455303Notes

Reaction equation

HRID 455303 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7]([NH:10][CH3:11])(=[O:9])=[O:8].C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C1COCC1>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7](=[O:9])(=[O:8])[NH:10][CH3:11])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86667513HCID 86667513, compound

Product 1

HCID 86667512HCID 86667512, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-hydroxy-N-methylpentane-1-sulfonamide (Example 21; 6.4 mmol) and triethyl amine (19.2 mmol) in THF (15 ml) was added para toluenesulfonyl chloride (5.9 mmol) in THF (5 ml) at room temperature and the reaction mixture was stirred for 10 hours. The reaction mixture was washed by saturated NaHCO3 solution and then brine. The organic layer was dried over MgSO4, filtered off and concentrated. The residue was purified by flash column chromatography (SiO2; eluent: petroleum ether/ethyl acetate from 100/0 to 50/50) to give the pure title compound (0.9 gr; 41% yield.

Workup

  1. washThe reaction mixture was washed by saturated NaHCO3 solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered off
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (SiO2; eluent: petroleum ether/ethyl acetate from 100/0 to 50/50)

Sources & evidence

ORD record
ord-0f1da45c1ab846ebba6ba7fa72a683b5
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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