Sodium Hydroxide → (3aS, 6aR)-hexahydro-2-oxo-1,3-dibenzylthieno[3,4-d]imidazol-4-ylpentanoic acid

HRID 10764Notes

Reaction equation

HRID 10764 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]2[CH2:14][S:15][C:16](=[C:17]([CH2:21][CH2:22][CH3:23])[C:18]([OH:20])=[O:19])[C@H:4]2[N:3]1[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[Na+].[H][H]>O.[Pd]>[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:5]2[CH2:14][S:15][CH:16]([CH:17]([CH2:21][CH2:22][CH3:23])[C:18]([OH:20])=[O:19])[C@H:4]2[N:3]1[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 86591115cis-2-oxo-1,3-dibenzyl-hexahydro-1H-thieno[3,4-d]imidazol-4-ylidenepentanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 86591114(3aS, 6aR)-hexahydro-2-oxo-1,3-dibenzylthieno[3,4-d]imidazol-4-ylpentanoic acidYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

100 g of (3aS, 6aR)hexahydro2-oxo-1,3-dibenzylthieno[3,4-d]imidazol-4-ylidenepentanoic acid (formula I) are dissolved in 340 ml of water at 40° C., where the pH is set to 8.7 using aqueous sodium hydroxide solution. 25% by weight of 5% Pd/C are added to the solution. The mixture is subsequently hydrogenated at an H2 pressure of 3 bar and 100° C. until the takeup of hydrogen is complete. The catalyst is filtered off after cooling. The solution is set to pH=6.0 using hydrochloric acid and extracted with 300 ml of xylene. The aqueous phase is subsequently extracted again with 100 ml of xylene. The organic phases are combined, and the solvents are evaporated, leaving 96 g of (3aS, 6aR)-hexahydro-2-oxo-1,3-dibenzylthieno[3,4-d]imidazol-4-ylpentanoic acid (formula II) as a pale-yellow oil.

Workup

  1. filtrationThe catalyst is filtered off
  2. temperatureafter cooling
  3. extractionextracted with 300 ml of xylene
  4. extractionThe aqueous phase is subsequently extracted again with 100 ml of xylene
  5. customthe solvents are evaporated

Sources & evidence

ORD record
ord-4c3d7276b6f746199ab6434788921770
Source dataset
uspto-grants-2006_08
Patent number
US07094905B2

Reaction notes

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