Diethyl (ethoxymethylene)malonate → Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate

HRID 8471

Reaktionsgleichung

Reaktionsgleichung von HRID 8471
[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[NH:4][C@@H:5]([CH3:8])[CH2:6][OH:7].C(O[CH:18]=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>>[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[N:4]([CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C@@H:5]([CH3:8])[CH2:6][OH:7]

Komponenten

3

Edukt 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

Produkt 1

HCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonateAusbeute 78 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the compound (103 mg) obtained in Example 51 was added diethyl ethoxymethylenemalonate (127 mg). Then the obtained mixture was stirred for 1 hour while heating to 100° C. under atmospheric pressure. Further, it was stirred at the same temperature for 1.5 hour under reduced pressure and then under atmospheric pressure for additional 16 hours. By analyzing reversed phase HPLC with the use of the compound of Example 63 as a specimen, the obtained product corresponded to 142 mg (78%) of the title compound.

Aufarbeitung

  1. stirringFurther, it was stirred at the same temperature for 1.5 hour under reduced pressure
  2. waitunder atmospheric pressure for additional 16 hours

Quellen und Nachweise

ORD-Eintrag
ord-426f633887724b84bb4638f94290938a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087778B2

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