2-Cyanoethyl tetraisopropylphosphorodiamidite → N-biotinyl-aminopropyl 2-cyanoethyl N,N-diisopropylphosphoramidite

HRID 1165364

Reaktionsgleichung

Reaktionsgleichung von HRID 1165364
[C:1]([NH:16][CH:17](O)[CH2:18][CH3:19])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:14]2[C@@H:9]([NH:10][C:11]([NH:13]2)=[O:12])[CH2:8][S:7]1.N1[C-]=NN=N1.C([NH2+]C(C)C)(C)C.[CH:33]([N:36]([CH:50]([CH3:52])[CH3:51])[P:37](N(C(C)C)C(C)C)[O:38][CH2:39][CH2:40][C:41]#[N:42])([CH3:35])[CH3:34].C(=O)(O)[O-:54].[Na+]>CN(C=O)C>[CH:33]([N:36]([CH:50]([CH3:52])[CH3:51])[P:37]([O:38][CH2:39][CH2:40][C:41]#[N:42])[O:54][CH2:19][CH2:18][CH2:17][NH:16][C:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:14]2[C@@H:9]([NH:10][C:11]([NH:13]2)=[O:12])[CH2:8][S:7]1)([CH3:35])[CH3:34]

Komponenten

6

Edukt 4

HCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 516892Sodium BicarbonateHCID 131716340N-biotinylaminopropanolHCID 178458033HCID 178458033, Verbindung

Produkt 1

HCID 15085419N-biotinyl-aminopropyl 2-cyanoethyl N,N-diisopropylphosphoramidite

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 150 mg of N-biotinylaminopropanol (2b) in 5 ml of dry DMF was added 65 mg of diisopropylammonium tetrazolide and 0.300 ml of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite. The resulting solution was stirred at room temperature for 1.0 hr and then poured onto 50 ml of 5% aqueous sodium bicarbonate. The mixture was extracted with two 50 ml portions of methylene chloride, and the combined extracts were washed with 5% sodium bicarbonate and brine, dried over sodium sulfate, and evaporated to afford the crude product as a thick oil. This was dissolved in 2 ml of dry methylene chloride affording a solution that was added dropwise to 30 ml of rapidly stirring petroleum ether. The colorless precipitate which formed was collected by suction filtration under argon, affording after drying at room temperature under vacuum 151 mg (60%) of a colorless solid.

Aufarbeitung

  1. extractionThe mixture was extracted with two 50 ml portions of methylene chloride
  2. washthe combined extracts were washed with 5% sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7164f27389e64b539be65359be962472
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04908453

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