2-Cyanoethyl tetraisopropylphosphorodiamidite → Diisopropylamino-5-(carbomethoxy)pentyloxy-2-cyanoethoxy phosphine

HRID 274988

Reaktionsgleichung

Reaktionsgleichung von HRID 274988
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].N1[C-]=NN=N1.C([NH2+]C(C)C)(C)C.[CH:23]([N:26]([P:30](N(C(C)C)C(C)C)[O:31][CH2:32][CH2:33][C:34]#[N:35])[CH:27]([CH3:29])[CH3:28])([CH3:25])[CH3:24]>ClCCl>[CH:23]([N:26]([P:30]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:10])[O:31][CH2:32][CH2:33][C:34]#[N:35])[CH:27]([CH3:28])[CH3:29])([CH3:24])[CH3:25]

Komponenten

5

Edukt 3

HCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 3083855Hexanoic acid, 6-hydroxy-, methyl esterHCID 178458033HCID 178458033, Verbindung

Produkt 1

HCID 20089729Diisopropylamino-5-(carbomethoxy)pentyloxy-2-cyanoethoxy phosphine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 0.786 g (5.37 mmole) of methyl-6-hydroxyhexanoate and 0.48 g (2.8 mmole) of diisopropylammonium tetrazolide in 25 ml of dichloromethane were added dropwise 1.62 g (5.37 mmole) of bis(diisopropyl amino)-2-cyanoethyoxyphosphine (Aldrich). The resulting solution was stirred at 25° C. for 2 hours and extracted with phosphate buffer at pH 7. Drying over magnesium sulfate and fast chromatography on silica gel (40% ethylacetate-hexanes, trace triethylamine) yielded the diisopropylamino-5-(carbomethoxy)pentyloxy-2-cyanoethoxy phosphine linking group as a colorless oil (1.30 g: 70%).

Aufarbeitung

  1. extractionextracted with phosphate buffer at pH 7
  2. dry with materialDrying over magnesium sulfate and fast chromatography on silica gel (40% ethylacetate-hexanes, trace triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-2389888995ce4186becda88fbe432b3f
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391723

Verknüpfte Notizen

Wird geladen…