Diisopropylethylamine → HCID 59643248, Verbindung

HRID 2251475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251475
[NH2:1][CH2:2][CH2:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[F:27][C:28]([F:42])([F:41])[C:29]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:30]=1[CH2:31]Br>ClCCl>[F:27][C:28]([F:41])([F:42])[C:29]1[CH:36]=[C:35]([C:37]([F:40])([F:38])[F:39])[CH:34]=[CH:33][C:30]=1[CH2:31][NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 21320401Methyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoate

Produkt 1

HCID 59643248HCID 59643248, VerbindungAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoate (Biochim. Biophys. Acta 1997, 1339 (2), 321–330) (2 g; 8.44 mmol) in dichloromethane (20 ml) was treated with DIEA (1.47 ml; 8.44 mmol) and 2,4-bis-trifluoromethyl-benzyl bromide (2.59 g; 8.44 mmol). After stirring at rt overnight, the reaction mixture was concentrated and partitioned between ethyl acetate and saturated Na2CO3 solution. The organic phase was washed with Na2CO3 solution and brine, dried over sodium sulfate and concentrated. Purification by flash chromatography on silica gel using an ethyl acetate-hexane mixture (10–50%) afforded the title compound (2.0 g; 51% yield).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and saturated Na2CO3 solution
  3. washThe organic phase was washed with Na2CO3 solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel using an ethyl acetate-hexane mixture (10–50%)

Quellen und Nachweise

ORD-Eintrag
ord-dbf12498bfc5464d97f156fbd8d71744
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319104B2

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