Hydrochloric Acid → Voglibose

HRID 1858406ノート

反応式

HRID 1858406 の反応式
[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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 68294SerinolHCID 443630HCID 443630、化合物

生成物 1

HCID 444020Voglibose

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1ab5b41f94544c8c853eff64fce4c340
出典データセット
uspto-grants-2000_11
特許番号
US06150568

反応ノート

読み込み中…