N-[(carbobenzyloxycarbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester → N-(valinyl)-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

HRID 634946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634946
C(C([NH:13][C@H:14]([C:18]([NH:20][CH:21]([CH:30]([OH:43])[CH2:31][O:32][C:33]1[C:38]([F:39])=[C:37]([F:40])[CH:36]=[C:35]([F:41])[C:34]=1[F:42])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19])[CH:15]([CH3:17])[CH3:16])=O)(OCC1C=CC=CC=1)=O>CO.[Pd]>[NH2:13][C@H:14]([C:18]([NH:20][CH:21]([CH:30]([OH:43])[CH2:31][O:32][C:33]1[C:34]([F:42])=[C:35]([F:41])[CH:36]=[C:37]([F:40])[C:38]=1[F:39])[CH2:22][C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])=[O:19])[CH:15]([CH3:17])[CH3:16]

Komponenten

4

Edukt 1

HCID 86584481N-[(carbobenzyloxycarbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

Produkt 1

HCID 86584482N-(valinyl)-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl esterAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of N-[(carbobenzyloxycarbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (6.12 g, 10.50 mmol) in MeOH (300 ml) was added 10% palladium on carbon (0.92 g) at room temperature. The reaction was stirred for 3 hours under hydrogen (1 atm), then filtered through a pad of celite. The filter cake was washed with MeOH. The filtrate was concentrated in vacuo to provide the titled product as a viscous yellow oil (4.69 g, 10.30 mmol, 98%). MS C20H20N2O5, [M+Na]+ =475, [M−H]− =451.

Aufarbeitung

  1. filtrationfiltered through a pad of celite
  2. washThe filter cake was washed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-536a8a4a504a45d39df4311d97bfa54d
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184244B2

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