4-Toluenesulfonyl chloride → HCID 86601559, compound

HRID 458293Notes

Reaction equation

HRID 458293 reaction equation
[CH2:1]([O:3][CH:4]([O:30][CH2:31][CH3:32])[CH2:5][C@@H:6]([CH2:9][O:10][C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:7][OH:8])[CH3:2].C(N([CH2:38][CH3:39])CC)C.[C:40]1(C)[CH:45]=C[C:43]([S:46](Cl)(=[O:48])=[O:47])=[CH:42][CH:41]=1>C(Cl)Cl>[C:38]1([CH3:39])[C:43]([S:46]([O:8][CH2:7][C@H:6]([CH2:9][O:10][C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:30][CH2:31][CH3:32])(=[O:48])=[O:47])=[CH:42][CH:41]=[CH:40][CH:45]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 12149282HCID 12149282, compound

Product 1

HCID 86601559HCID 86601559, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
46 °C

Procedure

The product of Example 31, step a) (26.21 g, 0.057 mol) was dissolved in methylene chloride (75 mL) and charged into a 250 mL 3 necked flask equipped with a magnetic stir bar, condenser, N2 inlet, and temperature probe. Triethylamine (14.4 g) was added followed by p-toluenesulfonyl chloride (16.3 g). The flask was purged with N2 and heated to reflux (46° C.). The reaction was stirred at reflux 6 hours. The reaction was cooled to room temperature. Water (10 mL) was added and the reaction was stirred vigorously for 16 hours. The reaction mixture was poured into a 1 L separatory funnel containing ethyl acetate (350 mL) and water (350 mL). The organic layer was separated and washed with 7% (w/w) aq. sodium bicarbonate (100 mL). The organic layer was then washed with 23% (w/w) aq. sodium chloride (100 mL). The organic layer was dried with Na2SO4 and filtered. The solution was concentrated to give the desired product (29.4 g) as an oil that formed a wet solid when cooled to room temperature.

Workup

  1. customequipped with a magnetic stir bar, condenser, N2 inlet
  2. customThe flask was purged with N2
  3. temperatureheated
  4. temperatureat reflux 6 hours
  5. temperatureThe reaction was cooled to room temperature
  6. additionWater (10 mL) was added
  7. stirringthe reaction was stirred vigorously for 16 hours
  8. additionThe reaction mixture was poured into a 1 L separatory funnel
  9. additioncontaining ethyl acetate (350 mL) and water (350 mL)
  10. customThe organic layer was separated
  11. washwashed with 7% (w/w) aq. sodium bicarbonate (100 mL)
  12. washThe organic layer was then washed with 23% (w/w) aq. sodium chloride (100 mL)
  13. dry with materialThe organic layer was dried with Na2SO4
  14. filtrationfiltered
  15. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-6c8d007b26914109bde763c63cc8ea31
Source dataset
uspto-grants-2007_03
Patent number
US07189849B2

Reaction notes

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