Acetonitrile → SNOB 1 reagent

HRID 19469

Reaktionsgleichung

Reaktionsgleichung von HRID 19469
O[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].O[N:18]1C(=O)[CH2:21][CH2:20][C:19]1=O.C(N)C=C.[Al].C(#N)C>CN(C=O)C.O>[CH2:19]([NH:18][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)[CH:20]=[CH2:21]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 7853AllylamineHCID 5359268AluminumHCID 86743017n-Hydroxysuccinimide biotin3×

Produkt 1

HCID 87497786SNOB 1 reagent

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In an argon-purged 100 ml flask, biotin-N-hydroxy-succinimide (251 mg, 0.735 mmol; Compound 1, Sigma-Aldrich) was dissolved in 26.7 ml dry DMF and mixed with allylamine (50 μl, 0.668 mmol; Nacalai Tesque, Inc., Japan), followed by stirring at room temperature with the flask covered with aluminum foil for light shielding. The progress of the reaction was monitored by C18 reversed-phase HPLC (HPLC conditions; column: μ-Bondsphere φ19×150 mm (Waters); mobile phase: 20% acetonitrile in H2O; elution speed: 10 ml/min; detection: UV absorption (200 nm)). At 3 hours after initiation of the reaction, it was confirmed that the source material biotin-N-hydroxysuccinimide was almost completely converted into Compound 2. This reaction solution was used directly in the subsequent reaction.

Aufarbeitung

  1. customIn an argon-purged 100 ml flask
  2. washelution speed
  3. customdetection: UV absorption (200 nm))
  4. customAt 3 hours after initiation of the reaction, it
  5. customThis reaction solution was used directly in the subsequent reaction

Quellen und Nachweise

ORD-Eintrag
ord-995e1f5daf82450bb2905b34d4defa5a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745417B2

Verknüpfte Notizen

Wird geladen…