Dicyclohexylcarbodiimide → N-Hydroxysulfosuccinimide

HRID 2305998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305998
[Na].[OH:2][N:3]1[C:7](=[O:8])[CH2:6][CH:5]([S:9]([OH:12])(=[O:11])=[O:10])[C:4]1=[O:13].C1(N=C=NC2CCCCC2)CCCCC1>CC(N(C)C)=O>[OH:2][N:3]1[C:7](=[O:8])[CH2:6][CH:5]([S:9]([OH:12])(=[O:10])=[O:11])[C:4]1=[O:13]

Komponenten

4

Edukt 2

HCID 10868DicyclohexylcarbodiimideHCID 86222747sodium N-hydroxysulfosuccinimide

Produkt 1

HCID 133909N-Hydroxysulfosuccinimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

L-DM1-TPA (6, 2 mg 0.002 mmol) was dissolved in dimethylacetamide (0.25 mL), to which N-hydroxysulfosuccinimide sodium salt (1.0 mg, 0.0046 mmol) and dicyclohexylcarbodiimide (1.0 mg, 0.0048 mmol) were added. After 3 hours, 0.5 mL of diisopropyl alcohol was added and the resulting precipitate was removed by filtration. HPLC analysis (Vydac C-18 column, 10×250 C18 column, 30° C., flow rate 4.75 mL/min, 50 mM triethylammonium formate pH 3.8 buffer with a linear methanol gradient (30% to 90% over 30 minutes) of the filtrate showed two major peaks, one for unreacted L-DM1-TPA at 22 min and one for L-DM1-TPA sulfosuccinimidyl ester at 19 min. The compound eluting at 19 min was isolated and analyzed by mass spectrometry showing that it had the expected peak consistent with the disodiated molecular ion (M++2Na) of 3a, m/e 1091.4. Further fragmentation of the 1091.4 ion gave predictable daughter ions, m/e 1073.4 (M++2Na—H2O ), 874.4 (M++2Na-sodiated N-hydroxysulfosuccinimide).

Aufarbeitung

  1. additionwere added
  2. customthe resulting precipitate was removed by filtration
  3. customVydac C-18 column, 10×250 C18 column, 30° C., flow rate 4.75 mL/min, 50 mM triethylammonium formate pH 3.8
  4. custombuffer with a linear methanol gradient (30% to 90% over 30 minutes) of the filtrate
  5. customat 22 min
  6. waitone for L-DM1-TPA sulfosuccinimidyl ester at 19 min
  7. washThe compound eluting at 19 min
  8. customwas isolated

Quellen und Nachweise

ORD-Eintrag
ord-ec2c358087bc4087aae8386a56e38454
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06441163B1

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