Benzoyl Peroxide → 8-Hydroxymethylriboflavin

HRID 343742Notes

Reaction equation

HRID 343742 reaction equation
[C:1](OOC(=O)C1C=CC=CC=1)(=[O:8])C1C=CC=CC=1.[Br-].[Br-].O1CCOCC1.[CH3:27][C:28]1[C:33](C)=[CH:32][C:31]2[N:35]([CH2:45][CH:46]([O:62]C(C)=O)[CH:47]([O:58]C(C)=O)[CH:48]([O:54]C(C)=O)[CH2:49][O:50]C(C)=O)[C:36]3[C:43](=[N:44][C:30]=2[CH:29]=1)[C:41](=[O:42])[NH:40][C:38](=[O:39])[N:37]=3>O1CCOCC1>[CH3:27][C:28]1[C:33]([CH2:1][OH:8])=[CH:32][C:31]2[N:35]([CH2:45][C@@H:46]([OH:62])[C@@H:47]([OH:58])[C@@H:48]([OH:54])[CH2:49][OH:50])[C:36]3[C:43](=[N:44][C:30]=2[CH:29]=1)[C:41](=[O:42])[NH:40][C:38](=[O:39])[N:37]=3

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 941862,3,4,5-Tetra-O-acetyl-1-deoxy-1-(4-hydroxy-7,8-dimethyl-2-oxobenzo(g)pteridin-10(2H)-yl)pentitolHCID 222259191,4-Dioxane dibromide

Product 1

HCID 1938668-Hydroxymethylriboflavin

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Synthesis of 8α-hydroxyriboflavin was carried out by the method of McCormick (21). Briefly, riboflavin was added to a solution of acetic acid: acetic anhydride (1:1) and the yellow solution was stirred at room temperature for 24 hours. Tetra-acetylriboflavin (TAR) was extracted from the aqueous reaction mixture with CHCl3, followed by extraction with water and evaporation to give a yellow residue of essentially pure TAR. Dibenzoyl peroxide and dioxane dibromide in dioxane were added to a solution of TAR in dioxane, and the solution was refluxed. The crude bromo-TAR was separated from the reaction mixture on a C-18 Semi-Prep HPLC column (Beckman). The bromo-TAR was hydrolyzed to yield 8α-hydroxyriboflavin, which was separated by HPLC (System Gold, Beckman) through a linear gradient from 0.5% trifluoroacetic acid (TFA) in water to 0.5% TFA in acetonitrile for 50 minutes at a flow rate of 4 ml/minute.

Workup

  1. temperaturethe solution was refluxed
  2. customThe crude bromo-TAR was separated from the reaction mixture on a C-18 Semi-Prep HPLC column (Beckman)

Sources & evidence

ORD record
ord-ad9ee7beae994e01942dde36a7e3020b
Source dataset
uspto-grants-1999_01
Patent number
US05863776

Reaction notes

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