Hydrochloric Acid → AO 128

HRID 1858406Notes

Reaction equation

HRID 1858406 reaction equation
[CH2:1]1[C@:7]([OH:10])([CH2:8][OH:9])[C@@H:6]([OH:11])[C@H:5]([OH:12])[C@@H:4]([OH:13])[C:2]1=O.[NH2:14][CH:15]([CH2:18][OH:19])[CH2:16][OH:17].Cl>CN(C=O)C.CO>[CH2:1]1[C@:7]([OH:10])([CH2:8][OH:9])[C@@H:6]([OH:11])[C@H:5]([OH:12])[C@@H:4]([OH:13])[C@H:2]1[NH:14][CH:15]([CH2:18][OH:19])[CH2:16][OH:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68294SerinolHCID 443630HCID 443630, compound

Product 1

HCID 444020AO 128

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5 mmol of valiolone and 5 mmol of 2-amino-1,3-propanediol in 25 mL DMF or methanol is added a catalytic amount of HCl. After 1 hour at room temperature, 2.5 mmol of solid Na(CN)BH3 is added and the reaction mixture is stirred over night at room temperature. The reaction mixture is then concentrated under reduced pressure and the residue is dissolved in water and applied to a Dowex 50 (H+) column. The column is washed with water and the product is eluted with 0.5 N NH4OH. After concentrating the eluate, the residue is dissolved in water and applied successively first to a Amberlite CG-50 (NH4+) or Diaion WK-100 (NH4+) and then a Dowex 1 (OH-) column and each time the product is eluted with water to give voglibose.

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in water
  3. washThe column is washed with water
  4. washthe product is eluted with 0.5 N NH4OH
  5. concentrationAfter concentrating the eluate, the residue
  6. dissolutionis dissolved in water
  7. wash(NH4+) and then a Dowex 1 (OH-) column and each time the product is eluted with water

Sources & evidence

ORD record
ord-1ab5b41f94544c8c853eff64fce4c340
Source dataset
uspto-grants-2000_11
Patent number
US06150568

Reaction notes

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