p-Toluenesulfonic acid monohydrate → HCID 58591305, compound

HRID 132097Notes

Reaction equation

HRID 132097 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([NH:18][CH2:19][CH:20]([OH:35])[CH:21]([NH:31][C:32](=[O:34])[CH3:33])[CH2:22][C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=3)[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([NH:18][CH2:19][CH:20]([OH:35])[CH:21]([NH:31][C:32](=[O:34])[CH3:33])[CH2:22][C:23]3[CH:24]=[C:25]([F:30])[CH:26]=[C:27]([F:29])[CH:28]=3)[CH2:17][CH2:16][C:11](=[O:12])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11753221HCID 11753221, compound

Product 1

HCID 58591305HCID 58591305, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

Compound 18 (0.4 g, 0.78 mmol), p-Toluenesulfonic acid monohydrate (TsOH) (0.16 g, 0.84 mmol), and poly(Ethylene glycol) (8.9 g, 143.4 mmol) were added to 25 mL benzene. The reaction was heated to 100° C. for 30 min. The benzene was removed under reduced pressure and fresh benzene was added. The resulting mixture was treated with saturated NaHCO3 and extracted CH2Cl2. The organic layer was washed with brine and dried with MgSO4, filtered and concentrated under reduced pressure providing 0.4 g of Compound 19.

Workup

  1. customThe benzene was removed under reduced pressure and fresh benzene
  2. additionwas added
  3. additionThe resulting mixture was treated with saturated NaHCO3
  4. extractionextracted CH2Cl2
  5. washThe organic layer was washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74d34a4b92174de5a7d72f28e1c64574
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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