Water → HCID 67735164, compound

HRID 742363Notes

Reaction equation

HRID 742363 reaction equation
[CH3:1][N:2]([CH3:29])[C:3](=[O:28])[NH:4][C:5]1[C:13]([CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][C:19]([O:21]C)=[O:20])=[C:12]([CH2:24][CH3:25])[C:11]([CH3:26])=[C:10]2[C:6]=1[C:7](=[O:27])[O:8][CH2:9]2.O.O.[OH-].[Li+]>CO>[CH3:29][N:2]([CH3:1])[C:3](=[O:28])[NH:4][C:5]1[C:13]([CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:12]([CH2:24][CH3:25])[C:11]([CH3:26])=[C:10]2[C:6]=1[C:7](=[O:27])[O:8][CH2:9]2

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86749566HCID 86749566, compound

Product 1

HCID 67735164HCID 67735164, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.3 g (0.74 mmol) of methyl (E)-6-[1,3-dihydro-4-(3,3-dimethylureido)-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl]-4-methyl-4-hexenoate in 7.4 ml of 4:1 methanol:water is added 0.13 g (2.96 mmol) of lithium hydroxide monohydrate. The solution is heated at 50°-60° C. for 4 hours. Upon cooling, the reaction is partitioned between aqueous sodium hydrogen sulfate and ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, and concentrated to give (E)-6-[1,3-dihydro-4-(3,3-dimethylureido)-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl]-4-methyl-4-hexenoic acid.

Workup

  1. temperatureThe solution is heated at 50°-60° C. for 4 hours
  2. temperatureUpon cooling
  3. customthe reaction is partitioned between aqueous sodium hydrogen sulfate and ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d0e65c5700346a6b2d4cc8c15a066f4
Source dataset
uspto-grants-1996_09
Patent number
US05554612

Reaction notes

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