Sodium Hydroxide → HCID 57633744, Verbindung

HRID 2109100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2109100
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:10][CH:11]([CH3:16])[C:12]([O:14]C)=[O:13])=[CH:5][C:4]=1[C:22]([F:25])([F:24])[F:23])#[N:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:17][C:18]([F:21])([F:19])[F:20])[CH2:10][CH:11]([CH3:16])[C:12]([OH:14])=[O:13])=[CH:5][C:4]=1[C:22]([F:23])([F:25])[F:24])#[N:2]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 57633720HCID 57633720, Verbindung

Produkt 1

HCID 57633744HCID 57633744, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A solution of methyl 3-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]-2-methylpropanoate (0.056 g, 0.152 mmol) in 1:1 THF/MeOH (6 mL) was treated with NaOH (1N, 1 mL, 1.0 mmol) and heated at 75° C. for 30 min. Upon cooling, the mixture was partitioned between EtOAc and 0.1N HCl. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (0.050 g, 94% yield): 1H NMR (400 MHz, CDCl3) δ 7.66 (d, J=8.8 Hz, 1H), 7.06 (d, J=2.6 Hz, 1H), 6.92 (dd, J=8.8, 2.6 Hz, 1H), 4.20-4.02 (m, 2H), 3.87 (dd, J=15.6, 9.0 Hz, 1H), 3.56 (dd, J=15.6, 5.0 Hz, 1H), 3.0-2.9 (m, 1H), 1.29 (d, J=7.1 Hz, 3H).

Aufarbeitung

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between EtOAc and 0.1N HCl
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-244f915f041d40f383a3ba9fb9f16de4
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514470B2

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