Hydrogen Peroxide → 1H-Thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, 5,5-dioxide, (3aS,4S,6aR)-

HRID 1527717Notes

Reaction equation

HRID 1527717 reaction equation
[OH:1]C(CCCC[C@H]1[C@@H]2[C@@H](NC(N2)=O)CS1)=O.OO.[OH:19][C:20]([CH2:22][CH2:23][CH2:24][CH2:25][C@H:26]1[C@@H:35]2[C@@H:30]([NH:31][C:32]([NH:34]2)=[O:33])[CH2:29][S:27]1=[O:28])=[O:21]>CC(O)=O>[O:33]=[C:32]1[NH:34][C@H:35]2[C@H:30]([CH2:29][S:27](=[O:1])(=[O:28])[C@H:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:20]([OH:19])=[O:21])[NH:31]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 83833(3aS,4S,6aR)-4-(4-Carboxybutyl)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-5-ium-5-olateHCID 171548Biotin

Product 1

HCID 838631H-Thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, 5,5-dioxide, (3aS,4S,6aR)-Yield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of Sachon et al.,42 D-biotin (83, 0.304 g, 1.24 mmol) was suspended in AcOH (3.0 mL) and then H2O2 (35% in H2O, 1.0 mL) was added at room temperature. The suspension became a colorless, clear solution after 10 min at room temperature, and biotin sulfoxide began to precipitate after 5 hours. The reaction was stirred at room temperature for 65 hours, then filtered. The white filter cake was then washed with 20 mL of ether and dried under reduced pressure to provide 89 as a white solid (0.298 g, 1.08 mmol, 87%).

Workup

  1. customafter 10 min
  2. customat room temperature
  3. customto precipitate after 5 hours
  4. filtrationfiltered
  5. washThe white filter cake was then washed with 20 mL of ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-29ed544e7f7e41b1b405df41afd27d0c
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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