4-Toluenesulfonyl chloride → HCID 87114009, compound

HRID 452976Notes

Reaction equation

HRID 452976 reaction equation
[CH3:1][C@H:2]1[O:6][CH:5]([CH2:7][OH:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>ClCCl>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:8][CH2:7][CH:5]2[CH2:4][CH2:3][C@@H:2]([CH3:1])[O:6]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 66643150HCID 66643150, compound

Product 1

HCID 87114009HCID 87114009, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 64A (4.0 g, 25.8 mmol) in dichloromethane (100 mL) were added triethylamine (10.8 mL, 77.0 mmol) and p-toluenesulfonyl chloride (4.9 g, 25.8 mmol). The reaction mixture was stirred at room temperature overnight and then washed with water (50 mL) and brine (50 mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-25% ethyl acetate in hexanes) to provide 3.5 g (50%) of the title compound. MS (DCI+) m/z 288 (M+NH4)+.

Workup

  1. washwashed with water (50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7027dfc886d3404ca10896a159eaee83
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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