Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-nitrobenzyl)-L-glutamate → Di-tert-butyl (4S)-4-(4-aminobenzyl)-N-(tert-butoxycarbonyl)-L-glutamate

HRID 591260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591260
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C@H:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][C@@H:9]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:25][CH:24]=1

Komponenten

4

Edukt 1

HCID 89136291Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-nitrobenzyl)-L-glutamate

Produkt 1

HCID 89136283Di-tert-butyl (4S)-4-(4-aminobenzyl)-N-(tert-butoxycarbonyl)-L-glutamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To 2.35 g (4.3 mmol) di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-(4-nitrobenzyl)-L-glutamate in 50 mL methanol and under argon atmosphere palladium (10% on charcoal) was added and the suspension hydrogenated overnight at room temperature. The reaction mixture was filtered, the solvent evaporated and the residue was chromatographed on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Aufarbeitung

  1. customthe suspension hydrogenated overnight
  2. customat room temperature
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent evaporated
  5. customthe residue was chromatographed on silica gel using a hexane/ethyl acetate gradient
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3afdcd2b3bb3487390f10fab5d309632
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238631B2

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