p-Toluenesulfonic acid → Methyl (4E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

HRID 1735793Notes

Reaction equation

HRID 1735793 reaction equation
[OH:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:19])/[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:9]([O:20][CH3:21])[C:8]([CH3:22])=[C:7]2[C:3]=1[C:4](=[O:23])[O:5][CH2:6]2.[C:24]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:19])/[CH2:14][CH2:15][C:16]([O:18][CH3:24])=[O:17])=[C:9]([O:20][CH3:21])[C:8]([CH3:22])=[C:7]2[C:3]=1[C:4](=[O:23])[O:5][CH2:6]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 446541Mycophenolic Acid

Product 1

HCID 6478685Methyl (4E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoateYield 1,243.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 15.1 g (47.1 mmol) of (E)-6-(1,3-dihydro-4-hydroxy-6- methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid (mycophenolic acid) and 0.7 g (3.7 mmol) of p-toluenesulfonic acid in 400 ml of methanol was allowed to stand at room temperature for 3 days. The mixture was concentrated under reduced pressure to approximately 75 ml and then partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic phase was further washed with brine and then dried over sodium sulfate. Concentration of the organic phase under reduced pressure gave 15.4 g (46.0 mmol, 98%) of methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate as a white solid, mp 104°-105° C.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure to approximately 75 ml
  2. custompartitioned between aqueous sodium bicarbonate and ethyl acetate
  3. washThe organic phase was further washed with brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-ccf882b910624007bf47c24ea22e107b
Source dataset
uspto-grants-1996_07
Patent number
US05538969

Reaction notes

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