Reaction #1435697

ord-9770eb78dbcb438ab2b66941e528ff74

Reaction equation

CCO
ethanol
Cl.N[C@@H](CS)C(=O)O
cysteine hydrochloride
OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O
maltose
CCO
Ethanol
c1ccncc1
pyridine
→
O=C(O)C1CSC(C(O)C(O)C(OC2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(O)CO)N1
2-(1,2,4,5-Tetrahydroxy-3-Glucopyranosyloxypentyl) Thiazolidine-4-Carboxylic acid

Reactants

CCO
ethanol
Cl.N[C@@H](CS)C(=O)O
cysteine hydrochloride
OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O
maltose
CCO
Ethanol
c1ccncc1
pyridine

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.WAITthe solution was left
  2. 2
    Otherwas formed
  3. 3
    OtherThe solvent was removed by decantation
  4. 4
    workup.DISSOLUTIONthe precipitate was dissolved in 100 ml of water
  5. 5
    OtherAfter the insoluble matters were removed by filtration
  6. 6
    Othercondensed to about 30 ml
  7. 7
    workup.WAITthe solution was then left
  8. 8
    Otherto stand in a refrigerator overnight
  9. 9
    FiltrationThe produced crystals were collected by filtration
  10. 10
    workup.DISSOLUTIONThe crystals were then dissolved in water again
  11. 11
    Otherthe insoluble matters were removed by filtration
  12. 12
    Othercondensed, and ethanol
  13. 13
    workup.ADDITIONwas added to the solution
  14. 14
    Otherrecrystallization
  15. 15
    FiltrationThe produced crystals were collected by filtration
  16. 16
    Otherdried under reduced pressure
  17. 17
    Otherto obtain 2.2 g of a white powder (molar yield based on cysteine: 4.9%)

Procedure

17.56 Grams (100 mmol) of cysteine hydrochloride and 34.20 g (100 mmol) of maltose were dissolved in 35 ml of pure water, 8.36 ml (100 mmol) of pyridine was then added thereto, and the resulting solution was stirred at room temperature for 72 hours. 300 Milliliters of ethanol was added to the stirred solution, and the solution was left to stand in a refrigerator, whereby a paste-like precipitate was formed. The solvent was removed by decantation, and the precipitate was dissolved in 100 ml of water. After the insoluble matters were removed by filtration, the remaining solution was condensed to about 30 ml. Ethanol was continuously added to the condensed solution until a precipitate was about to appear, and the solution was then left to stand in a refrigerator overnight. The produced crystals were collected by filtration. The crystals were then dissolved in water again, the insoluble matters were removed by filtration, the resulting solution was condensed, and ethanol was added to the solution to cause recrystallization. The produced crystals were collected by filtration and dried under reduced pressure to obtain 2.2 g of a white powder (molar yield based on cysteine: 4.9%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07211285B2uspto-grants-2007_05