Trifluoroacetic acid → Valienamine

HRID 902402Notes

Reaction equation

HRID 902402 reaction equation
C[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1[NH:33][C@@H:34]1[C@H:39]([OH:40])[C@@H:38]([OH:41])[C@H:37]([OH:42])[C:36]([CH2:43][OH:44])=[CH:35]1.C(O)(C(F)(F)F)=O>>[CH:35]1[C@H:34]([NH2:33])[C@H:39]([OH:40])[C@@H:38]([OH:41])[C@H:37]([OH:42])[C:36]=1[CH2:43][OH:44]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 444254HCID 444254, compound

Product 1

HCID 193758ValienamineYield 110.6%

Procedure

1 g of a pure acarbose derivative (monosaccharide and trisaccharide) were place into 10% TFA solution at 5% final concentration. While putting pressure using an autoclave, at reaction temperature of 121° C., it was reacted for 30 minutes to 1 hour, followed by removal of TFA and water. Then, by using ion-exchange resins for purification, 0.46 g and 0.30 g of valienamine were obtained, respectively.

Workup

  1. concentrationconcentration
  2. customat reaction temperature of 121° C., it
  3. customwas reacted for 30 minutes to 1 hour
  4. customfollowed by removal of TFA and water
  5. customfor purification, 0.46 g

Sources & evidence

ORD record
ord-0897763175734954910b16e4350d130f
Source dataset
uspto-grants-2008_04
Patent number
US07365192B2

Reaction notes

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