Triethylamine → 4-[6-(2,2,2-Trifluoro-acetylamino)-hexanoylamino]-benzenesulfonyl azide

HRID 1714079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1714079
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[N+:12]=[N-:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:21][C:22]([F:35])([F:34])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32])=[O:24]>CN(C)C=O>[F:21][C:22]([F:34])([F:35])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[N+:12]=[N-:13])(=[O:9])=[O:10])=[CH:4][CH:3]=1)=[O:32])=[O:24]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 112064084-Aminobenzenesulfonyl azideHCID 114365186-(Trifluoroacetamido)hexanoyl chloride

Produkt 1

HCID 866261244-[6-(2,2,2-Trifluoro-acetylamino)-hexanoylamino]-benzenesulfonyl azide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To 0.57 g (3 mmol) of para-amino-benzenesulfonyl azide dissolved in 5 mL dimethylformamide was added 0.9 mL (6 mmol) triethylamine, then the (2,2,2-trifluro-acetylamino)-hexanoyl chloride dissolved in 10 mL dimethylformamide was added dropwise. The mixture turned brown and was stirred under argon for 24 hrs. Solvent was evaporated, and the remaining oil was dissolved in 10 mL dichloromethane and left at room temperature for 1 hr. The precipitate was filtrated and the solution was evaporated to yield 1.10 g crude oil. The obtained compound was directly used in oligonucleotide synthesis.

Aufarbeitung

  1. additionwas added dropwise
  2. customSolvent was evaporated
  3. dissolutionthe remaining oil was dissolved in 10 mL dichloromethane
  4. waitleft at room temperature for 1 hr
  5. filtrationThe precipitate was filtrated
  6. customthe solution was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-223c7ad2ab5a4003b0395fa342dfae5c
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795423B2

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