Ethyl Acetate → (S)-2-[4-(2-fluoro-3-vinyl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester

HRID 19164

Reaktionsgleichung

Reaktionsgleichung von HRID 19164
CC1(C)O[C@H](CN2C=CC(N[C:14](=[O:35])[C@@H:15]([N:20]3[CH2:24][C:23]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28](Br)[C:27]=4[F:33])=[CH:22][C:21]3=[O:34])[CH2:16][CH:17]([CH3:19])[CH3:18])=N2)CO1.C([Sn](CC[CH2:50][CH3:51])(CCCC)C=C)CCC.[C:52](OCC)(=[O:54])[CH3:53]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:52]([O:54][C:14](=[O:35])[C@@H:15]([N:20]1[CH2:24][C:23]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH:50]=[CH2:51])[C:27]=2[F:33])=[CH:22][C:21]1=[O:34])[CH2:16][CH:17]([CH3:18])[CH3:19])[CH3:53]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 44252757(S)-2-[4-(3-bromo-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1 H-pyrazol-3-yl]-amide

Produkt 1

HCID 66894709(S)-2-[4-(2-fluoro-3-vinyl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl esterAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of (S)-2-[4-(3-bromo-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester (prepared as in Example 128, 0.624 g, 1.51 mmol), tetrakis(triphenylphosphine)palladium(0) (0.200 g, 0.17 mmol) in N,N-dimethylformamide (7 mL) was added tributyl(vinyl)tin (0.652 g, 2.05 mmol) and the resulting mixture stirred at 80° C. for 14 h. The mixture was taken up in ethyl acetate and dilute hydrochloric acid and separated. The organic phase was washed with, saturated sodium bicarbonate solution, a saturated sodium chloride solution and dried over sodium sulfate. The mixture was filtered, evaporated and the residue purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 50 g, 10% to 50% ethyl acetate/hexanes) which afforded (S)-2-[4-(2-fluoro-3-vinyl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester (0.400 g, 73%) as a clear oil.

Aufarbeitung

  1. customdilute hydrochloric acid and separated
  2. washThe organic phase was washed with, saturated sodium bicarbonate solution
  3. dry with materiala saturated sodium chloride solution and dried over sodium sulfate
  4. filtrationThe mixture was filtered
  5. customevaporated
  6. customthe residue purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 50 g, 10% to 50% ethyl acetate/hexanes) which

Quellen und Nachweise

ORD-Eintrag
ord-10c6ae687e6e4b76b041e8313a666d71
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741327B2

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