Methylhydrazine → HCID 86740486, compound

HRID 653318Notes

Reaction equation

HRID 653318 reaction equation
C1(=O)[N:5]([C@H:6]2[C@@H:9](/[CH:10]=[CH:11]/[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C:7]2=[O:25])C(=O)C2=CC=CC=C12.CNN>C(COC)OC>[NH2:5][C@H:6]1[C@@H:9](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]([Si:18]([C:21]([CH3:23])([CH3:22])[CH3:24])([CH3:20])[CH3:19])[C:7]1=[O:25]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 86740485HCID 86740485, compound

Product 1

HCID 86740486HCID 86740486, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In 5 ml of dimethoxyethane is suspended 440 mg of cis-3-phthalimido-4-(E)-styryl-1-(tert-butyldimethylsilyl)-2-oxoazetidine and after addition of 0.26 ml of methylhydrazine, the mixture is stirred at room temperature for 30 minutes. The solvent is then distilled off under reduced pressure and the residue is dissolved by addition of 5 ml of methylene chloride and allowed to stand overnight. The precipitate is filtered off and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography [eluent:chloroform-ethyl acetate (6:4)] to give an oil of cis-3-amino-4-(E)-styryl-1-(tert-butyldimethylsilyl)-2-oxoazetidine. This oil is dissolved in 10 ml of tetrahydrofuran and under ice-cooling and stirring, 0.2 ml of triethylamine is added, followed by addition of 0.212 g of 2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetyl chloride hydrochloride. The mixture is stirred under ice-cooling for 10 minutes and then at room temperature for 30 minutes, after which the reaction mixture is shaken with ethyl acetate and water. The ethyl acetate layer is taken, washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is purified by silica gel column chromatogtaphy [eluent:chloroform-ethyl acetate (7:3)] and crystallized from ether to give cis-[2-(2-chloroacetamido-4 -thiazolyl)-2-methoxyiminoacetamido]-4-(E)-styryl-1-(tert-butyldimethylsilyl)-2-oxoazetidine (sin-isomer), melting at 228°-231° C. (decomp.).

Workup

  1. distillationThe solvent is then distilled off under reduced pressure
  2. dissolutionthe residue is dissolved by addition of 5 ml of methylene chloride
  3. waitto stand overnight
  4. filtrationThe precipitate is filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography [eluent:chloroform-ethyl acetate (6:4)]

Sources & evidence

ORD record
ord-37fd294dc741421fb16ba75ac2af321c
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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