1,4-Dioxane hydrochloride → HCID 56605368, compound

HRID 64418Notes

Reaction equation

HRID 64418 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:9][CH2:10][CH3:11])[CH:4]([OH:8])[C:5]([OH:7])=[O:6].Cl.O1CCOC[CH2:14]1>CO>[NH2:2][C@@H:3]([CH2:9][CH2:10][CH3:11])[C@@H:4]([OH:8])[C:5]([O:7][CH3:14])=[O:6].[NH2:2][C@@H:3]([CH2:9][CH2:10][CH3:11])[C@H:4]([OH:8])[C:5]([O:7][CH3:14])=[O:6]

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86713428(3S)-3-amino-2-hydroxyhexanoic acid hydrochloride

Product 2

HCID 56605368HCID 56605368, compoundHCID 86639467HCID 86639467, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1 g of (3S)-3-amino-2-hydroxyhexanoic acid hydrochloride in 10 mL of methanol was added 10 mL of a 4 M hydrogen chloride/dioxane solution, followed by stirring overnight, and the solvent was evaporated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution and chloroform were added thereto to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 425 mg of methyl (2R,3S)-3-amino-2-hydroxyhexanoate and 130 mg of methyl (2S,3S)-3-amino-2-hydroxyhexanoate.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionA saturated aqueous sodium hydrogen carbonate solution and chloroform were added
  3. customa layer separation operation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f7ce0d4cd681410fba10f5dd96dff5f7
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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