Methylhydrazine → HCID 70390924, compound

HRID 653294Notes

Reaction equation

HRID 653294 reaction equation
[CH2:1]([O:5][C:6]([C@H:8]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])[C:10](=[O:23])[C@H:9]1[N:24]1C(=O)C2=CC=CC=C2C1=O)=[O:7])[CH2:2][CH2:3][CH3:4].CNN>C(Cl)Cl>[CH2:1]([O:5][C:6]([C@H:8]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])[C:10](=[O:23])[C@H:9]1[NH2:24])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 70390605HCID 70390605, compound

Product 1

HCID 70390924HCID 70390924, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 19 g of cis-1-(2,4-dimethoxybenzyl)-3-phthalimido-2-oxoazetidine-4-carboxylic acid n-butyl ester in 190 ml of methylene chloride is added 3.7 g of methyl hydrazine. The mixture is stirred overnight at room temperature. The reaction mixture is subjected to filtration, and the filtrate is concentrated under reduced pressure. To the residue is added ethyl acetate, and the insolubles are removed by filtration. The filtrate is subjected to extraction twice, with 100 ml each of 1N--HCl. The extracts are neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The extract is washed with an aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure to yield 12 g (87.5%) of cis-3-amino-1-(2,4-dimethoxybenzyl)-2-oxoazetidine-4-carboxylic acid n-butyl ester as oily product.

Workup

  1. filtrationThe reaction mixture is subjected to filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. additionTo the residue is added ethyl acetate
  4. customthe insolubles are removed by filtration
  5. extractionThe filtrate is subjected to extraction twice
  6. extractionextracted with ethyl acetate
  7. washThe extract is washed with an aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. customfollowed by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-c4f5b7db39344cc08f5331bf16b0be81
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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