Cyanogen Bromide → N2-(tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl ester

HRID 1975903

Reaktionsgleichung

Reaktionsgleichung von HRID 1975903
[C:1]([O:5][C:6](=[O:30])[C@H:7]([CH2:16][CH2:17][CH2:18][NH:19][C:20](OCC1C=CC=CC=1)=O)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[N:31]#CBr.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.[Pd].CCOCC>[C:1]([O:5][C:6](=[O:30])[C@H:7]([CH2:16][CH2:17][CH2:18][NH:19][C:20]#[N:31])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 10047875tert-Butyl (2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoate

Produkt 1

HCID 11141515N2-(tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl esterAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 3283Diethyl EtherLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

To a solution of 6.1 g (14.4 mmol) N5-((Benzyloxy)carbonyl)-N2-(tert-butoxycarbonyl)-L-ornithine tert-butyl ester in 100 mL ethyl acetate was added 1.0 g 10% palladium on carbon. The suspension was shaken at 22° C. under 50 psi H2 for 45 minutes in a 500 mL Parr bottle. The catalyst was removed by filtration through celite. The resulting solution was concentrated to yield a crude oil. The oil was dissolved into 50 mL of diethyl ether and added dropwise to a 0° C. stirred solution of 1.52 g (14.3 mmol) of cyanogen bromide in 30 mL ether. The solution was stirred for 2 h, poured into aqueous sodium bicarbonate, and extracted with ether. The ether solution was dried (magnesium sulfate), concentrated, and purified by silica gel chromatography (100 g, 130-400 mesh silica gel). Elution with a gradient of ethyl acetate in hexanes (30%-60%) gave 3.0 g (67% yield) N2-(tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl ester as an oil.

Aufarbeitung

  1. customThe catalyst was removed by filtration through celite
  2. concentrationThe resulting solution was concentrated
  3. customto yield a crude oil
  4. additionadded dropwise to a 0° C.
  5. stirringThe solution was stirred for 2 h
  6. extractionextracted with ether
  7. dry with materialThe ether solution was dried (magnesium sulfate)
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (100 g, 130-400 mesh silica gel)
  10. washElution with a gradient of ethyl acetate in hexanes (30%-60%)

Quellen und Nachweise

ORD-Eintrag
ord-5d478177235648db8a1abb9e88814f81
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06225305B1

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