Reaction #2186171

ord-a8be21481f7143808e7e7e67e9b718fd

Reaction equation

N[C@@H](C[13c]1ccccc1)C(=O)O
(1-13C]-phenylalanine
CC(O)COC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8COCC(C)O)O[C@@H]7COCC(C)O)O[C@@H]6COCC(C)O)O[C@@H]5COCC(C)O)O[C@@H]4COCC(C)O)O[C@@H]3COCC(C)O
hydroxypropyl-β-cyclodextrin
→
CC(O)COC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8COCC(C)O)O[C@@H]7COCC(C)O)O[C@@H]6COCC(C)O)O[C@@H]5COCC(C)O)O[C@@H]4COCC(C)O)O[C@@H]3COCC(C)O.N[C@@H](C[13c]1ccccc1)C(=O)O
(1-13C] phenylalanine hydroxypropyl-β-cyclodextrin

Reactants

N[C@@H](C[13c]1ccccc1)C(=O)O
(1-13C]-phenylalanine
CC(O)COC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8COCC(C)O)O[C@@H]7COCC(C)O)O[C@@H]6COCC(C)O)O[C@@H]5COCC(C)O)O[C@@H]4COCC(C)O)O[C@@H]3COCC(C)O
hydroxypropyl-β-cyclodextrin

Reagents

None

Solvents

O
water

Conditions

Temperature
85°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureto cool to 25° C.
  2. 2
    Otherno precipitation of phenylalanine
  3. 3
    Otherat 25° C
  4. 4
    workup.ADDITIONOn the other hand, if 299 mg of (1-13C]-phenylalanine only was added to 5 ml of distilled water
  5. 5
    Temperatureheated to 85° C.
  6. 6
    workup.DISSOLUTIONto dissolve
  7. 7
    Otherphenylalanine was precipitated when this solution
  8. 8
    Temperatureto cool to 25° C
  9. 9
    TemperatureThe increase of solubility of phenylalanine in the presence of hydroxypropyl-β-cyclodextrin

Procedure

To 5 ml of distilled water, 299 mg of (1-13C]-phenylalanine and 1818, mg hydroxypropyl-β-cyclodextrin (in a molar ratio of 1:1) were added and heated to 85° C. to make a solution. Thus, a solution of (1-13C] phenylalanine/hydroxypropyl-β-cyclodextrin inclusion complex was prepared wherein when this solution was allowed to cool to 25° C., no precipitation of phenylalanine was observed while the solubility of phenylalanine is 148 mg/5 ml at 25° C. On the other hand, if 299 mg of (1-13C]-phenylalanine only was added to 5 ml of distilled water and heated to 85° C. to dissolve, phenylalanine was precipitated when this solution was allowed to cool to 25° C. The increase of solubility of phenylalanine in the presence of hydroxypropyl-β-cyclodextrin confirmed the formation of (1-13C]-phenylalanine/hydroxypropyl-β-cyclodextrin inclusion complex.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07569208B2uspto-grants-2009_08