Methylhydrazine → HCID 131716510, compound

HRID 1709380Notes

Reaction equation

HRID 1709380 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@H:8]([N:11]2C(=O)C3=CC=CC=C3C2=O)[C@@H:7]1[C:22]([CH3:29])=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].CNN>C(Cl)Cl>[NH2:11][C@H:8]1[C@@H:7]([C:22]([CH3:29])=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:6]([CH2:5][C:4]2[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:3]=2[O:2][CH3:1])[C:9]1=[O:10]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 131716511HCID 131716511, compound

Product 1

HCID 131716510HCID 131716510, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

37.0 g (77.3 mmol) of ethyl rac-cis-1-(2,4-dimethoxybenzyl)-β-methyl-4-oxo-3-phthalimido-2-azetidineacrylate are dissolved in 500 ml of methylene chloride and the solution is treated with 8.2 ml (0.15 mmol) of N-methylhydrazine at 30° C. for 48 hours. The mixture is filtered and the filtrate is evaporated. The residue is taken up in ethyl acetate and filtered. The filtrate is extracted with 200 ml of aqueous hydrochloric acid and the aqueous phase is separated, neutralized with saturated aqueous sodium bicarbonate solution and extracted twice with 200 ml of methylene chloride each time. After drying and evaporation, the crude colourless product is isolated. There are obtained 25.1 g (93%) of ethyl rac-cis-3-amino-1-(2,4-dimethoxybenzyl)-β-methyl-2-oxo-4-azetidineacrylate of melting point 89°-93° C.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated
  3. filtrationfiltered
  4. extractionThe filtrate is extracted with 200 ml of aqueous hydrochloric acid
  5. customthe aqueous phase is separated
  6. extractionextracted twice with 200 ml of methylene chloride each time
  7. customAfter drying
  8. customevaporation
  9. customthe crude colourless product is isolated

Sources & evidence

ORD record
ord-208572383e7d40d6b47b82f69540b820
Source dataset
uspto-grants-1990_08
Patent number
US04948898

Reaction notes

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