Trifluoroacetic acid → Sodium 3,6-disulfonaphthylthiourea

HRID 635774

Reaktionsgleichung

Reaktionsgleichung von HRID 635774
FC(F)(F)C(O)=O.C[N:9](C)CC=C.[S:14]([C:18]1[CH:19]=[C:20]([N:32]=[C:33]=[S:34])[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:23][CH:22]=2)([OH:17])(=[O:16])=[O:15].[Na:35]>ClCCl.O>[S:14]([C:18]1[CH:19]=[C:20]([NH:32][C:33]([NH2:9])=[S:34])[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([S:28]([OH:31])(=[O:29])=[O:30])=[CH:23][CH:22]=2)([OH:17])(=[O:16])=[O:15].[Na:35]

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 75082N,N-DimethylallylamineHCID 86584464sodium 3,6-Disulfonapthylisothiocyanate

Produkt 1

HCID 86584463Sodium 3,6-disulfonaphthylthiourea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (2 ml) was added to a suspension of BHAlyslys2lys4lys8DBL16 (73 mg; 0.01 mmol) in dry dichloromethane (2 ml) under nitrogen A vigorous evolution of gas was observed for a short time and the resulting solution was stirred at room temperature for two hours and then concentrated. The residual syrup was dissolved in water (5 ml), the solution passed through a column of Amberlite IRA-401 (OH) and the filtrate concentrated to give BHAlyslys2lys4lys8lys16 as a viscous oil. The oil was redissolved in water (5 ml) and N,N-dimethyl-N-allylamine buffer (pH 9.5; 3 ml) added. Solid sodium 3,6-disulfonapthylisothiocyanate (234 mg; 0.60 mmol) was then added and the resulting solution heated under nitrogen at 53° for two hours and then cooled. The solution was concentrated and the brownish solid residue purified by gel filtration (Sephadex LH20; water). The pure fractions were combined, passed through a column of Amberlite IR 120(Na) and freeze dried to give BHAlyslys2lys4lys8lys16 terminated with 32 sodium 3,6-disulfonapthylthiourea groups as a fluffy off-white solid (119 mg). 1H nmr (D2O): δ 1.0-2.0; 3.18; 3.43; 4.31; 7.22; 7.80; 7.89; 8.25. 13C nmr (D2O): δ 27.2; 32.4; 35.3; 43.7; 49.0; 58.5; 63.6; 128.4; 129.1; 131.4; 136.1; 136.6; 138.6; 139.0; 145.1; 145.6; 178.4; 184.8; 186.7.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residual syrup was dissolved in water (5 ml)
  3. concentrationthe filtrate concentrated
  4. customto give BHAlyslys2lys4lys8lys16 as a viscous oil
  5. temperaturethe resulting solution heated under nitrogen at 53° for two hours
  6. temperaturecooled
  7. concentrationThe solution was concentrated
  8. filtrationthe brownish solid residue purified by gel filtration (Sephadex LH20; water)
  9. customdried
  10. customto give BHAlyslys2lys4lys8lys16
  11. customterminated with 32 sodium 3,6-disulfonapthylthiourea groups as a fluffy off-white solid (119 mg)

Quellen und Nachweise

ORD-Eintrag
ord-94ee823599694de9be5e0ba93722ab5f
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06190650B1

Verknüpfte Notizen

Wird geladen…