Hydrazine hydrate (1:1) → HCID 66985760, compound

HRID 2064672Notes

Reaction equation

HRID 2064672 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:14](=O)[CH3:15])[C:6](=O)[CH2:7][O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:2].O.[NH2:19][NH2:20]>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:5]1[C:6]([CH2:7][O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[N:19][NH:20][C:14]=1[CH3:15])=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 85826160HCID 85826160, compound

Product 1

HCID 66985760HCID 66985760, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-acetyl-4-tert-butoxy-3-oxo-butyric acid ethyl ester [0.325 g, Reference Example 46] in acetic acid (3 ml) was added hydrazine hydrate (71 μL). The mixture was stirred at ambient temperature for 16 hours and then evaporated to remove the acetic acid. The residue was dissolved in ethyl acetate and the solution was washed with 5% sodium hydrogen carbonate solution, then with water, then dried over magnesium sulfate, and then evaporated to yield 3-tert-butyloxymethyl-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.258 g) as a yellow oil which was used without further purification. LC-MS (METHOD B): RT=3.22 minutes; 241 (M+H)+.

Workup

  1. customevaporated
  2. customto remove the acetic acid
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with 5% sodium hydrogen carbonate solution
  5. dry with materialwith water, then dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-8b2c63d953b44369808704f41c421ad3
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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