HCID 69734264, Verbindung → HCID 86589157, Verbindung

HRID 1062900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062900
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5]([C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[C:10]([NH:12][C@@H:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:14](OC)=[O:15])=[O:11])=[O:6])[CH2:2][CH3:3]>C1(C)C=CC=CC=1>[CH2:25]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[C:10]([NH:12][C@@H:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH:14]=[O:15])=[O:11])=[O:6])[CH2:26][CH3:27]

Komponenten

3

Edukt 1

HCID 69734264HCID 69734264, Verbindung

Produkt 1

HCID 86589157HCID 86589157, VerbindungAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Methyl(2S)-2-({3-[(dipropylamino)carbonyl]benzoyl}amino)-4-methylpentanoate (1.65 g, 4.4 mmol) in 20 mL of toluene under nitrogen is cooled to −78° C. To this is added, dropwise over 5 min, 11 mL of a 1 M solution of Dibal in toluene. The mixture is stirred an additional 6 minutes, and is then quenched by addition of 2 mL of methanol. The cold bath is removed and 20 mL of a Rochelle salt solution is added and vigorously stirred while the mixture warms to ambient temperature. The product is extracted into ether and the organic phase is washed successively with Rochelle salt solution, water, and brine. It is dried over Na2SO4, concentrated, and chromatographed over silica gel, eluting with 50% ethyl acetate in heptane, to afford the title compound as a colorless oil (0.79 g, 2.3 mmol, 52%). 1H NMR (CDCl3) δ 9.7 (s, 1H), 7.85 (m, 1H), 7.79 (s, 1H), 7.49 (m, 2H), 6.81 (d, J=7 Hz, 1H), 4.78 (m, 1H), 3.46 (br t, 2H), 3.15 (br t, 2H), 1.82 (m, 2H), 1.70 (m, 2H), 1.62-1.53 (m, 3H), 1.01 (m, 9H), 0.75 (br t, 3H).

Aufarbeitung

  1. additionTo this is added, dropwise over 5 min
  2. customis then quenched by addition of 2 mL of methanol
  3. customThe cold bath is removed
  4. addition20 mL of a Rochelle salt solution is added
  5. stirringvigorously stirred while the mixture
  6. customwarms to ambient temperature
  7. extractionThe product is extracted into ether
  8. washthe organic phase is washed successively with Rochelle salt solution, water, and brine
  9. dry with materialIt is dried over Na2SO4
  10. concentrationconcentrated
  11. customchromatographed over silica gel
  12. washeluting with 50% ethyl acetate in heptane

Quellen und Nachweise

ORD-Eintrag
ord-1a3aaafe4bac4fd887f35b6ec8a1cdad
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962934B2

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