4-Toluenesulfonyl chloride → HCID 86641123, compound

HRID 2191040Notes

Reaction equation

HRID 2191040 reaction equation
[CH3:1][O:2][CH:3]1[O:11][C@H:10]2[C@H:5]([O:6][C:7]([CH3:13])([CH3:12])[O:8][CH2:9]2)[C@H:4]1[OH:14].[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>N1C=CC=CC=1>[CH3:22][C:21]1[CH:23]=[CH:24][C:18]([S:15]([O:14][C@@H:4]2[C@H:5]3[O:6][C:7]([CH3:12])([CH3:13])[O:8][CH2:9][C@H:10]3[O:11][C@@H:3]2[O:2][CH3:1])(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 13833842HCID 13833842, compound

Product 1

HCID 86641123HCID 86641123, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Compound 35.3 (35.42 g, 174 mmol) was dissolved in anhydrous pyridine, cooled to 0° C. and then treated with tosyl chloride (52.96 g, 278 mmol). The mixture was stirred at r.t. for 16 h and the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2, and washed with 3×100 mL water. The organic layer was collected, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a reverse phase column chromatography eluting with 50% EtOAc in hexane to give compound 35.4 (57.88 g, 93% yield).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with 3×100 mL water
  4. customThe organic layer was collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washeluting with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-797d6ba24d134da790bc38a5ece58257
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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