p-Toluenesulfonic acid monohydrate → HCID 68957204, compound

HRID 2378067Notes

Reaction equation

HRID 2378067 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2(O)[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:7][CH2:6]1)=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:9]=2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:6][CH2:7]1)=[O:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 68956458HCID 68956458, compound

Product 1

HCID 68957204HCID 68957204, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
64 °C

Procedure

To a solution of the product of Step C, 1-[5-hydroxy-3-(4-methoxy-phenyl)-4-phenyl-4,5-dihydro-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester, (2354 g) in toluene (8 L) is added p-toluenesulfonic acid monohydrate (40.8 g.) The mixture is stirred at 64° C. for 6.5 hours and is subsequently filtered over Celite filter aid. The Celite cake is washed with toluene (2×1 L) and the filtrate is diluted with a mixture of isopropanol (6 L) and heptane (6 L) to form a precipitate. The precipitate is triturated to afford a solid. The solid is triturated in a mixture of isopropanol (6 L) and heptane (2 L) for 3.5 hours and is subsequently collected by filtration. The solid is dried to afford the synthetic intermediate 1-[3-(4-methoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester (889 g.)

Workup

  1. filtrationis subsequently filtered over Celite
  2. filtrationfilter aid
  3. washThe Celite cake is washed with toluene (2×1 L)
  4. additionthe filtrate is diluted with a mixture of isopropanol (6 L) and heptane (6 L)
  5. customto form a precipitate
  6. customThe precipitate is triturated
  7. customto afford a solid
  8. customThe solid is triturated in a mixture of isopropanol (6 L) and heptane (2 L) for 3.5 hours
  9. filtrationis subsequently collected by filtration
  10. customThe solid is dried

Sources & evidence

ORD record
ord-27730491928143cda448362fc68df035
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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