Potassium Bromide → HCID 24826226, compound

HRID 1951992Notes

Reaction equation

HRID 1951992 reaction equation
[Br-].[K+].[OH:3][CH2:4][C@H:5]1[O:10][C:9]([CH3:12])([CH3:11])[O:8][C@@H:7]([CH2:13][C:14]([N:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[O:15])[CH2:6]1.Cl[O-].[Na+]>C(Cl)Cl>[CH:4]([C@H:5]1[O:10][C:9]([CH3:11])([CH3:12])[O:8][C@@H:7]([CH2:13][C:14]([N:16]([CH:17]([CH3:19])[CH3:18])[CH:20]([CH3:21])[CH3:22])=[O:15])[CH2:6]1)=[O:3]

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 23665760Sodium HypochloriteHCID 68557098HCID 68557098, compound

Product 1

HCID 24826226HCID 24826226, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 gram of potassium bromide and 0.1 gram of 2,2,6,6-tetramethyl-1-piperidinyloxy free radical is added to the a solution of 25 grams of 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)-N,N-diisopropylacetamide in methylene chloride at 0-5° C. Added sodium hypochlorite to the above reaction mixture at 0-5° C. in 1 hour. Stirred the reaction for 30 minutes at 0-5° C. Quenched the reaction mixture with 10% sodium thio sulphate solution. Separated the organic and inorganic phases. Washed the organic layer with water. Dried the organic layer over sodium sulfate. Distilled the solvent completely under reduced pressure to get the title compound.

Workup

  1. customthe reaction for 30 minutes at 0-5° C
  2. customQuenched the reaction mixture with 10% sodium thio sulphate solution
  3. customSeparated the organic and inorganic phases
  4. washWashed the organic layer with water
  5. dry with materialDried the organic layer over sodium sulfate
  6. distillationDistilled the solvent completely under reduced pressure

Sources & evidence

ORD record
ord-480923a7a0e74cbabb928cfc051a056d
Source dataset
uspto-grants-2013_03
Patent number
US08404841B2

Reaction notes

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