Acetone → Hydrochloric Acid

HRID 1279545Notes

Reaction equation

HRID 1279545 reaction equation
[ClH:1].C([CH:5]1[NH:11][C:10](=[NH:12])[CH2:9][CH2:8][CH2:7][CH2:6]1)C=C.[NH+]1([O-])CC[O:16]CC1.S(=O)(O)[O-].[Na+].[CH3:25][C:26]([CH3:28])=[O:27]>C1COCC1.[Os](=O)(=O)(=O)=O>[ClH:1].[ClH:1].[NH:12]=[C:10]1[N:11]=[C:5]([CH2:25][CH:26]([OH:27])[CH2:28][OH:16])[CH:6]=[CH:7][CH:8]=[CH:9]1

Participants

8

Reactant 4

HCID 180AcetoneHCID 15900019Morpholine oxideHCID 23665763Sodium BisulfiteHCID 178439094HCID 178439094, compound

Product 2

HCID 313Hydrochloric AcidHCID 677797083-(7-Iminoazepin-2-yl)-1,2-propanediol, monohydrochloride

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To the product of EXAMPLE 108 in a mixture of acetone and THF is added osmium tetroxide. An aqueous solution of morpholine N-oxide is then added to the reaction and the mixture is stirred at room temperature over night. Sodium bisulfite is then added and this mixture is evaporated in vacuo to a solid. The solid is extracted with methanol thrice, and the combined extracts are evaporated in vacuo to a solid. This solid is dissolved in water and applied to a Dowex-50 ion exchange column (H+), which is eluted with water and then 0.2 N HCl to yield the title compound.

Workup

  1. customthis mixture is evaporated in vacuo to a solid
  2. extractionThe solid is extracted with methanol thrice
  3. customthe combined extracts are evaporated in vacuo to a solid
  4. dissolutionThis solid is dissolved in water
  5. washis eluted with water

Sources & evidence

ORD record
ord-3087ee088efc49fbb7c9620e3f3de58a
Source dataset
uspto-grants-2002_09
Patent number
US06448286B1

Reaction notes

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