Tetrahydrofuran → HCID 86605288, Verbindung

HRID 1348635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1348635
[CH2:1]([O:3][C:4](=[O:11])[C:5]([OH:10])([CH3:9])[C:6]([OH:8])=O)[CH3:2].O1CCCC1.[F:17][C:18]([F:25])([C:21]([F:24])([F:23])[F:22])[CH2:19][NH2:20].Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>>[CH2:1]([O:3][C:4](=[O:11])[C:5]([OH:10])([CH3:9])[C:6]([NH:20][CH2:19][C:18]([F:25])([F:17])[C:21]([F:24])([F:23])[F:22])=[O:8])[CH3:2]

Komponenten

6

Edukt 5

HCID 8028TetrahydrofuranHCID 790022,2,3,3,3-PentafluoropropylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13396337Propanedioic acid, 2-hydroxy-2-methyl-, 1-ethyl ester

Produkt 1

HCID 86605288HCID 86605288, VerbindungAusbeute 80 %

Versuchsvorschrift

To a solution of 2.08 g (12.8 mmol) 2-hydroxy-2-methyl-malonic acid monoethyl ester in 50 ml of tetrahydrofuran 1.39 g (12.8 mmol) of 2,2,3,3,3-pentafluoropropylamine, 2.51 g (12.8 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, 1.77 g (12.8 mmol) of 1-hydroxybenzotrizole hydrate and 4.48 ml (25.7 mmol) of N,N-diisopropyl-ethylamine were added. The mixture was stirred at room temperature for 18 h. Silicagel was added and the solvent was removed by distillation. The residue was purified by chromatography on silicagel (ethyl acetate/heptane=0:100 to 50:50) to yield 3.01 g (80%) of the title compound as white solid, MS m/e (%): 292.1 (M−H+, 100).

Aufarbeitung

  1. additionSilicagel was added
  2. customthe solvent was removed by distillation
  3. customThe residue was purified by chromatography on silicagel (ethyl acetate/heptane=0:100 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-3716e590135c40379ae776d4ea962179
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211573B2

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