HCID 70159551, Verbindung → HCID 70160425, Verbindung

HRID 842616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842616
[CH3:1][O:2][C:3]1[C:8]2[NH:9][CH:10]([CH2:13][N:14]([C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])C(=O)C)[CH2:11][O:12][C:7]=2[CH:6]=[CH:5][CH:4]=1>Cl>[CH3:1][O:2][C:3]1[C:8]2[NH:9][CH:10]([CH2:13][NH:14][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])[CH2:11][O:12][C:7]=2[CH:6]=[CH:5][CH:4]=1

Komponenten

3

Edukt 1

HCID 70159551HCID 70159551, Verbindung

Produkt 1

HCID 70160425HCID 70160425, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

The product from Example 7D (24.8 g, 72.9 mmol) in 2.0M HCl (500 mL) was refluxed for 16 hours, cooled, concentrated to a volume of 100 mL, basified to pH 14 with 50% NaOH and extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with ethyl acetate to provide two diastereomers, Rf 0.62 (ethyl acetate) and Rf 0.60 (ethyl acetate). 1H NMR (300 MHz, CDCl3, for Rf 0.62) δ1.35 (d, 3H), 1.55 (bs, 1H), 2.50-2.62 (m, 2H), 3.33 (bm, 1H), 3.73 (q, 1H), 3.83 (s, 3H), 3.90 (dd, 1H), 4.18 (dd, 1H), 4.35 (bs, 1H), 6.43 (m, 2H), 6.59 (t, 1H), 7.20-7.40 (m, 5H).

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated to a volume of 100 mL
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with ethyl acetate
  7. customto provide two diastereomers, Rf 0.62 (ethyl acetate) and Rf 0.60 (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2c33a5dc487b4335b86f9467efc08146
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376488B1

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