Hydrogen Peroxide → HCID 57429835, compound

HRID 656244Notes

Reaction equation

HRID 656244 reaction equation
C([C@@H]1COC(=O)N1[C:14]([C@H:16]1[C:18]2([CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH2:17]1)=[O:15])C1C=CC=CC=1.[OH-].[Li+].OO.S([O-])([O-])(=[O:30])=S.[Na+].[Na+]>O1CCCC1.O>[C@H:16]1([C:14]([OH:15])=[O:30])[C:18]2([CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH2:17]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24477Sodium ThiosulfateHCID 68652973(4R)-3-[(1R)-6-Oxaspiro[2.5]oct-1-ylcarbonyl]-4-(phenylmethyl)-2-oxazolidinone

Product 1

HCID 57429835HCID 57429835, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 3.700 g of (R)-4-benzyl-3-((R)-6-oxaspiro[2.5]-octane-1-carbonyl)oxazolidin-2-one in 20 ml of tetrahydrofuran/water 3:1 is cooled to 0° C. 0.608 g of lithium hydroxide and 1.95 ml of hydrogen peroxide (30% in water) are added to the solution, which is stirred at room temperature for 6 hours. Saturated aqueous sodium thiosulphate solution is added to the reaction mixture, which is then extracted with tert-butyl methyl ether. The aqueous phase is adjusted to pH 2 with 4M HCl and extracted with dichloromethane. The combined extracts are washed with brine, dried with sodium sulphate and evaporated. The title compound is obtained as a colourless liquid and is employed without further purification for the next stage. Rf=0.55 (dichloromethane-methanol-water-acetic acid 150:54:10:1); Rt=2.10 (Gradient I).

Workup

  1. extractionis then extracted with tert-butyl methyl ether
  2. extractionextracted with dichloromethane
  3. washThe combined extracts are washed with brine
  4. dry with materialdried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-cf2be54e0b0c4816ac0ce7a8b48b6e6f
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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