Carbonyl diazide → tert-Butyl amino(oxo)acetate

HRID 1071371Notes

Reaction equation

HRID 1071371 reaction equation
[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]

Participants

5

Reactant 2

HCID 18772028Carbonyl diazideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 12453830tert-Butyl amino(oxo)acetateYield 82.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ba8233fcd5d40cd8eb19e9684ca12e5
Source dataset
uspto-grants-2005_06
Patent number
US06906053B2

Reaction notes

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