Carbonyl diazide → tert-Butyl amino(oxo)acetate

HRID 2181061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181061
[N:1]([C:4](N=[N+]=[N-])=[O:5])=[N+]=[N-].[C:9]([O:13][C:14](OC([O-])=O)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CO.[OH-].[OH-].[Pd+2]>[C:14]([C:4]([NH2:1])=[O:5])([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15]

Komponenten

5

Edukt 2

HCID 18772028Carbonyl diazideHCID 22064466Tert-butyldicarbonate

Produkt 1

HCID 12453830tert-Butyl amino(oxo)acetateAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 19b (550 mg, 3.1 mmol)and t-butyldicarbonate (1.36 g, 6.2 mmol) in 50 mL of MeOH was placed in a Parr bottle with 20% Pd(OH)2 (200 mg) and hydrogenated under 50 psi of H2 for 6 hr. The reaction mixture was filtered through Celite in a sintered glass funnel and concentrated on a rotary evaporator. The residue was purified by silica gel chromatography to give 370 mg (55% yield) of Boc-amino ketone 19c.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite in a sintered glass funnel
  2. concentrationconcentrated on a rotary evaporator
  3. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2686b5fe071e4571b88efe2f81c589cc
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06890915B2

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