L-Aspartic Acid → (5-dibutylamino-naphthalene-1-sulfonyl)-L-aspartic acid

HRID 902584

Reaktionsgleichung

Reaktionsgleichung von HRID 902584
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].C([O-])(O)=O.[Na+].[CH2:15]([N:19]([CH2:34][CH2:35][CH2:36][CH3:37])[C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][CH:24]=[C:25]2[S:30](Cl)(=[O:32])=[O:31])[CH2:16][CH2:17][CH3:18]>O.CC(C)=O>[CH2:15]([N:19]([CH2:34][CH2:35][CH2:36][CH3:37])[C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][CH:24]=[C:25]2[S:30]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])(=[O:32])=[O:31])[CH2:16][CH2:17][CH3:18]

Komponenten

6

Edukt 3

HCID 5960L-Aspartic AcidHCID 191102Bansyl compoundHCID 516892Sodium Bicarbonate

Produkt 1

HCID 69279796(5-dibutylamino-naphthalene-1-sulfonyl)-L-aspartic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Two mmoles of aspartic acid and 4 mmoles of NaHCO3 were dissolved in 5 ml of water. A solution containing 1 mmol of 5-dibutylamino-naphthalene-1-sulfonyl chloride (Bansyl chloride, Purchased from TCI) in acetone was slowly added. More acetone was added until the solution was clear. The mixture was stirred overnight at room temperature and protected from light. Acetone was removed by flash evaporation and the remaining water solution was acidified to a of pH=4.5 to 5 by adding 2M citric acid. Then, NaCl was added until saturation and the solution was extracted with three portions of ethyl acetate (20 ml each). Extracts were combined, dried over MgSO4 and the solution was filtered. The solvent was removed and the residue was purified by liquid chromatography on a silica gel. A gradient of 0 to 5% methanol in dichloromethane was used as eluent. Fractions containing the desired product were combined and solvents removed. The residue was triturated in 1:1 ether: petroleum ether. The precipitate was filtered out and dried in vacuum overnight thus affording 5-dibutylamino-naphthalene-1-sulfonyl)-L-aspartic acid (NST705).

Aufarbeitung

  1. additionwas slowly added
  2. customAcetone was removed by flash evaporation
  3. additionby adding 2M citric acid
  4. additionThen, NaCl was added until saturation
  5. extractionthe solution was extracted with three portions of ethyl acetate (20 ml each)
  6. dry with materialdried over MgSO4
  7. filtrationthe solution was filtered
  8. customThe solvent was removed
  9. customthe residue was purified by liquid chromatography on a silica gel
  10. additionFractions containing the desired product
  11. customsolvents removed
  12. customThe residue was triturated in 1:1 ether
  13. filtrationThe precipitate was filtered out
  14. dry with materialdried in vacuum overnight thus affording 5-dibutylamino-naphthalene-1-sulfonyl)-L-aspartic acid (NST705)

Quellen und Nachweise

ORD-Eintrag
ord-bcd6dae67d894c5891d5e8382fd42bf3
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365223B2

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