Pyridine → HCID 86747746, compound

HRID 1463775Notes

Reaction equation

HRID 1463775 reaction equation
N1C=CC=CC=1.[NH2:7][C@@H:8]([C:12]([NH:14][C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][C:17]([OH:19])=[O:18])=[O:13])[CH:9]([CH3:11])[CH3:10].[O:23]=[CH:24][C@@H:25]([C@H:27]([C@@H:29]([C@@H:31]([CH2:33]O)[OH:32])[OH:30])[OH:28])[OH:26]>[Au].CO>[CH2:33]([NH:7][C@@H:8]([C:12]([NH:14][C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][C:17]([OH:19])=[O:18])=[O:13])[CH:9]([CH3:11])[CH3:10])[C:31]1([O:23][CH2:24][C@@H:25]([OH:26])[C@@H:27]([OH:28])[C@@H:29]1[OH:30])[OH:32]

Participants

6

Reactant 3

HCID 1049PyridineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 14426036HCID 14426036, compound

Product 1

HCID 86747746HCID 86747746, compound

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 887MethanolSolvent

Procedure

300 ml of pyridine and 3 l of methanol were added to 10 g of D-valyl-aspartic acid and 50 g of anhydrous D-glucose, and the stirred mixture was boiled for 2.5 hours. The reactants gradually dissolved during this time, and the reaction mixture assumed a yellow-gold color. After the reaction was complete, the mixture was concentrated in vacuo and further processed as described in Example 9. Freeze-drying resulted in 13.5 g of amorphous N-(1-deoxyfructopyranos-2-yl)-D-valyl-aspartic acid.

Workup

  1. dissolutionThe reactants gradually dissolved during this time
  2. concentrationthe mixture was concentrated in vacuo
  3. customFreeze-drying
  4. customresulted in 13.5 g of amorphous N-(1-deoxyfructopyranos-2-yl)-D-valyl-aspartic acid

Sources & evidence

ORD record
ord-172624d881c24548bcd033c0a001b5c5
Source dataset
uspto-grants-1994_04
Patent number
US05302582

Reaction notes

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