HCID 14460366, compound → HCID 14460371, compound

HRID 2371897Notes

Reaction equation

HRID 2371897 reaction equation
[N:1]([CH2:4][C:5]([C:8]1[O:14][CH:13]2[N:10]([C:11](=[O:15])[CH2:12]2)[C:9]=1[C:16]([O:18]CC1C=CC([N+]([O-])=O)=CC=1)=[O:17])([CH3:7])[CH3:6])=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd].O>[NH2:1][CH2:4][C:5]([C:8]1[O:14][CH:13]2[N:10]([C:11](=[O:15])[CH2:12]2)[C:9]=1[C:16]([OH:18])=[O:17])([CH3:7])[CH3:6]

Participants

6

Reactant 2

HCID 14460366HCID 14460366, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14460371HCID 14460371, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 21 mg (0.054 mmol) of p-nitrobenzyl 3-(2-azido-1,1-dimethylethyl)-7-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate in 1 ml of ethyl acetate is added via a syringe through a septum stopper to a prehydrogenated mixture, at 0° C., of 60 mg of palladium on charcoal (10%) in 1 ml of ethyl acetate and 0.7 ml of water. After a reaction time of 20 minutes, 5.7 ml of hydrogen have been taken up (theoretical amount 4.9 ml). The reaction mixture is filtered at 0° C., and the aqueous phase is washed twice with 2 ml of pre-cooled ethyl acetate. The aqueous phase contains 8.96 mg of the title compound. UV spectrum in H2O: λmax =271 nm (ε=5000)

Workup

  1. filtrationThe reaction mixture is filtered at 0° C.
  2. washthe aqueous phase is washed twice with 2 ml of pre-cooled ethyl acetate

Sources & evidence

ORD record
ord-7d8449212e2740f1b62f636c1510bc04
Source dataset
uspto-grants-1992_03
Patent number
US05096899

Reaction notes

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