Ethyl nitroacetate → Ammonia

HRID 1823759Notes

Reaction equation

HRID 1823759 reaction equation
[N+:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])([O-:3])=O.[C:10](OC(OC(OC(C)(C)C)=O)=O)(C)(C)[CH3:11]>CN(C)C1C=CN=CC=1>[C:5]([C:4]1[CH:11]=[CH:10][O:3][N:1]=1)([O:7][CH2:8][CH3:9])=[O:6].[NH3:1]

Participants

5

Reactant 2

HCID 69379Ethyl nitroacetateHCID 90495Di-tert-butyl dicarbonate

Product 2

HCID 222AmmoniaHCID 10034712ethyl isoxazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The starting acetylene was obtained as described in Example 118. The 3-carboethoxy isoxazole intermediate was obtained by cycloaddition of the nitrile oxide generated in situ from ethyl nitroacetate, di-t-butyldicarbonate and 4-dimethylaminopyridine. The amide was obtained from the 3-carboethoxy isoxazole intermediate by hydrolysis to the acid, conversion to the acyl chloride and reaction with ammonia. LRMS (ESI+) m/z: 358.0 (M−H+ C15H14F3N3O4 requires 358.0)

Sources & evidence

ORD record
ord-6503b2b600a943b6a56fad95b2f473eb
Source dataset
uspto-grants-2006_05
Patent number
US07041670B2

Reaction notes

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