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

HRID 742349Notes

Reaction equation

HRID 742349 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>[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:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[C:3]=1[CH2:24]/[CH:25]=[C:26](\[CH3:32])/[CH2:27][CH2:28][C:29]([O:31][CH3:33])=[O:30]

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-toluenesulfonyloxyisobenzofuran-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-21919ade202a452986e7464ecabbeb3b
Source dataset
uspto-grants-1996_09
Patent number
US05554612

Reaction notes

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