Acetic Acid → HCID 178451523, compound

HRID 448260Notes

Reaction equation

HRID 448260 reaction equation
[C:1]([C:3]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]([CH3:16])([CH3:15])[C:4]=1O)#[N:2].O.[NH2:19][NH2:20].CC(O)=O>C(O)C>[NH2:2][C:1]1[NH:20][N:19]=[C:4]2[C:5]([CH3:16])([CH3:15])[N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][C:3]=12

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 68926013tert-butyl 4-cyano-3-hydroxy-2,2-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 178451523HCID 178451523, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

32 g of tert-Butyl 4-cyano-3-hydroxy-2,2-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxylate (0.134 mol) were added to 430 ml of absolute ethanol. To this solution, 9 ml (0.18 mol) of hydrazine hydrate were added, followed by 12 ml of glacial AcOH (1.5 eq); The mixture was stirred at 60° C. for 48 hours, the ethanol was removed, the residue was taken up with 400 ml of sodium hydrogencarbonate solution, and extracted several times with ethyl acetate up to total extraction of the desired product. The organic phases were dried and evaporated. After purification by flash chromatography (eluent: CHCl3/EtOH 97/3) and trituration with a mixture of hexane/ethyl acetate 9/1, 25 g of title compound were obtained. Total yield 30.5 g (yield: 88%)

Workup

  1. customthe ethanol was removed
  2. extractionextracted several times with ethyl acetate
  3. extractionup to total extraction of the desired product
  4. customThe organic phases were dried
  5. customevaporated
  6. customAfter purification by flash chromatography (eluent: CHCl3/EtOH 97/3) and trituration
  7. additionwith a mixture of hexane/ethyl acetate 9/1

Sources & evidence

ORD record
ord-4e8a8315f9a8428681b9db58d833ebde
Source dataset
uspto-grants-2013_07
Patent number
US08481585B2

Reaction notes

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