HCID 67640328, Verbindung → HCID 67640683, Verbindung

HRID 399516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399516
[C:1]([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][C@H:10]([C:12]#[N:13])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][C@@H:10]([CH2:12][NH2:13])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH3:3])([CH3:4])[CH3:2]

Komponenten

4

Edukt 1

HCID 67640328HCID 67640328, Verbindung

Produkt 1

HCID 67640683HCID 67640683, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution (4S)-1-(tert-butyloxycarbonyl)-4-cyano-L-proline tert-butyl ester (470 mg, 1.59 mmol) in 90% ethanol (22 mL) was hydrogenated in the presence of 10% palladium-on-charcoal (225 mg) at 450 psi for 24 hours. The catalyst was removed by filtration through Celite, the filter washed with ethanol, and the combined filtrate and washings evaporated. Purification was achieved by flash silica gel chromatography eluting with 95:5:0.5 chloroform-methanol-ammonia; yield 284 mg (60%). 400 MHz 1H NMR (CD3OD): δ1.41-1.48 (3s, 18H); 1.58 (m, 1H); 2.28 (m, 1H); 2.48 (m, 1H); 2.66 (m, 2H); 3.05 (dd, 1H); 3.71 (dd, 1H); 4.12 (m, 1H).

Aufarbeitung

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter washed with ethanol
  3. customthe combined filtrate and washings evaporated
  4. customPurification
  5. washeluting with 95:5:0.5 chloroform-methanol-ammonia

Quellen und Nachweise

ORD-Eintrag
ord-aeb7fd57321348fdb99c27347f87fcdb
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821261

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