Di-tert-butyl (4R)-4-{[5-(benzyloxy)pyridin-2-yl]methyl}-N-(tert-butoxycarbonyl)-L-glutamate → Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamate

HRID 591283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591283
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:17][C@@H:18]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:23]([O:22][C:20]([NH:19][C@H:18]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:17][C@H:16]([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=1)[C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])=[O:21])([CH3:24])([CH3:25])[CH3:26]

Komponenten

4

Edukt 1

HCID 70957109Di-tert-butyl (4R)-4-{[5-(benzyloxy)pyridin-2-yl]methyl}-N-(tert-butoxycarbonyl)-L-glutamate

Produkt 1

HCID 70957058Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 610 mg (1.10 mmol) of di-tert-butyl (4R)-4-{[5-(benzyloxy)pyridin-2-yl]methyl}-N-(tert-butoxycarbonyl)-L-glutamate in methanol (35 mL) was added a 10% palladium on charcoal catalyst (29 mg), and the resulting suspension was stirred overnight under an atmosphere of hydrogen at room temperature. The catalyst was removed by filtration, and the filtrate was evaporated to give 500 mg of the pure target compound as colorless foam (98% yield).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5f595728438448d1b0546d0bbcb73b02
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238631B2

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