Methanol → HCID 68839439, compound

HRID 660600Notes

Reaction equation

HRID 660600 reaction equation
C([O:5][C:6](=[O:31])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[NH:17][S:16]2(=[O:22])=[O:21])=[C:11]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:10]=1)(C)(C)C.CO.[OH-].[Na+]>C1COCC1>[CH2:24]([O:23][C:11]1[CH:10]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:31])=[O:5])[CH:14]=[CH:13][C:12]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:22])=[O:21])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68842437HCID 68842437, compound

Product 1

HCID 68839439HCID 68839439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic acid tert-butyl ester (2.2 g, 5.18 mmol) in THF (14 mL)/MeOH (7 mL) is added 3.5 mL (20.7 mmol) of 6N NaOH solution and the mixture is stirred at RT for 18 h. The solvent is removed under reduced pressure and water is added to the residue. The mixture is acidified with 1N HCl and is extracted with methylene chloride. The organic phase is washed with water and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound as a reddish solid: ): (M−1)−=387.

Workup

  1. customThe solvent is removed under reduced pressure and water
  2. additionis added to the residue
  3. extractionis extracted with methylene chloride
  4. washThe organic phase is washed with water and brine
  5. dry with materialthen is dried over sodium sulfate
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-1dd63cb94ba4404e9391fdbbee1855ad
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…