Water → Methyl 6'-Desmethyl-4'-tosylmycophenolate

HRID 1735424Notes

Reaction equation

HRID 1735424 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6](=[O:12])[O:7][CH2:8]2)=[C:4]([O:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C:3]=1[CH2:24][CH:25]=[C:26]([CH3:32])[CH2:27][CH2:28][C:29]([OH:31])=[O:30].[C:33]1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(OCC)(=O)C>CO>[CH3:33][O:30][C:29](=[O:31])[CH2:28][CH2:27]/[C:26](/[CH3:32])=[CH:25]/[CH2:24][C:3]1[C:4]([O:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)(=[O:16])=[O:15])=[C:5]2[C:9](=[C:10]([CH3:11])[C:2]=1[OH:1])[CH2:8][O:7][C:6]2=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 536610776-(1,3-Dihydro-6-hydroxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoic acid

Product 1

HCID 10672181Methyl 6'-Desmethyl-4'-tosylmycophenolate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E) 6-(1,3-dihydro-6-hydroxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoic acid (23 g) and p-toluenesulfonic acid (0.8 g) in methanol (150 ml) was stirred for 18 hours then added to water and ethyl acetate. The organic layer was dried and evaporated and the residue was chromatographed on silica gel, eluting with hexane:ethyl acetate:methanol 40:58:2, to afford methyl (E) 6-(1,3-dihydro-6-hydroxy-7-methyl-3-oxo-4-p-toluene sulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate.

Workup

  1. customThe organic layer was dried
  2. customevaporated
  3. customthe residue was chromatographed on silica gel
  4. washeluting with hexane:ethyl acetate:methanol 40:58:2

Sources & evidence

ORD record
ord-8ecbe9b2e6384fe7b3a5a718f61069ef
Source dataset
uspto-grants-1996_07
Patent number
US05536747

Reaction notes

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