Diisopropylamine → Ethyl 2-(tert-butyl(2-(3-(thiazol-5-yl)prop-2-ynyloxy)ethyl)amino)-2-oxoacetate

HRID 1971689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971689
[C:1]([N:5]([CH2:13][CH2:14][O:15][CH2:16][C:17]#[CH:18])[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].Br[C:20]1[S:24][CH:23]=[N:22][CH:21]=1.C(NC(C)C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[NH4+].[Cl-]>O1CCOCC1.[Cu]I>[C:1]([N:5]([CH2:13][CH2:14][O:15][CH2:16][C:17]#[C:18][C:20]1[S:24][CH:23]=[N:22][CH:21]=1)[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Komponenten

8

Edukt 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 5460595-BromothiazoleHCID 58124829HCID 58124829, Verbindung

Produkt 1

HCID 58124907Ethyl 2-(tert-butyl(2-(3-(thiazol-5-yl)prop-2-ynyloxy)ethyl)amino)-2-oxoacetateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 390 mg of 11d, 290 mg of 5-bromothiazole, 400 μl of diisopropyl amine, 40 mg of PdCl2(PheCN)2, 20 mg of CuI and 300 μl of a 1M solution of tri-tert-butyl phosphine (in toluene) in 4 ml of degassed dioxane, was stirred under N2 for 16 hr. The mixture was poured into 20 ml of 5% aq. NH4Cl solution and extracted with ethyl acetate. The organic layer was dried, concentrated and the product was chromatographed over silica gel, using a gradient of heptane/ethyl acetate, to give 450 mg of 11e as a colorless oil; Rf 0.40 (heptane/ethyl acetate 1/1);

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe product was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-736a0c9105c949bbacba8c189952d8a3
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431564B2

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