Benzyl Bromide → HCID 54588054, compound

HRID 1698292Notes

Reaction equation

HRID 1698292 reaction equation
C(=O)([O-])O.[Na+].[CH2:6]([O:11][C:12]1[C@@H:17]([C@H:18]([CH2:20][OH:21])[OH:19])[O:16][C:14](=[O:15])[C:13]=1[OH:22])[CH:7]([CH2:9][OH:10])[OH:8].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[CH2:6]([O:11][C:12]1[C@@H:17]([C@H:18]([CH2:20][OH:21])[OH:19])[O:16][C:14](=[O:15])[C:13]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:7]([CH2:9][OH:10])[OH:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 672677953-Glyceryl ascorbate

Product 1

HCID 54588054HCID 54588054, compoundYield 127.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an argon atmosphere, water and sodium hydrogen carbonate (1.42 g) were added to 3-O-glyceryl ascorbic acid (1.42 g) obtained in Example 1, and the mixture was stirred at room temperature for 30 minutes. To the mixture, benzyl bromide (2.61 g) was added, and the resultant mixture was heated up to 50° C. and stirred for 2 hours. Thereafter, the mixture was concentrated under reduced pressure, then, dissolved in methanol. Then, the resultant solution was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and 6.13 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:10/3/0.4), and concentration was performed under reduced pressure to obtain to obtain 3-O-glyceryl-2-O-benzyl ascorbic acid (2.47 g).

Workup

  1. stirringstirred for 2 hours
  2. concentrationThereafter, the mixture was concentrated under reduced pressure
  3. dissolutiondissolved in methanol
  4. dry with materialThen, the resultant solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure, and 6.13 g of the resultant residue
  6. washElution
  7. concentrationwas performed with chloroform/methanol/water(volume ratio:10/3/0.4), and concentration
  8. customto obtain

Sources & evidence

ORD record
ord-1d46aa8b29dc4a1e9b8d87c9c84b4e72
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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