HCID 86740397, compound → HCID 86740451, compound

HRID 653278Notes

Reaction equation

HRID 653278 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:30][O:31][CH3:32])[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][O:20]C(=O)CCl)[N:17]([S:25]([O-:28])(=[O:27])=[O:26])[C:16]2=[O:29])=[O:13])[N:10]=1)=O.[Na+:33].CSC(=S)N.[Na]>O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:30][O:31][CH3:32])[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][OH:20])[N:17]([S:25]([O-:28])(=[O:26])=[O:27])[C:16]2=[O:29])=[O:13])[N:10]=1.[Na+:33]

Participants

4

Reactant 2

HCID 86740397HCID 86740397, compound2×HCID 86740453HCID 86740453, compound

Product 1

HCID 86740451HCID 86740451, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 2 ml of water is dissolved 70 mg of sodium cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-chloroacetoxymethyl-2-oxoazetidine-1-sulfonate (syn-isomer), and under ice-cooling and stirring, 39 mg of sodium monomethyldithiocarbamate is added. The mixture is stirred at room temperature for one hour. After addition of 10 mg of sodium monomethyldithiocarbamate, the mixture is stirred for 30 minutes. The reaction mixture is then filtered and the filtrate is washed with ether. The aqueous layer is chromatographed on an Amberlite XAD-II column and lyophilized to give sodium cis-3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-4-hydroxymethyl-2-oxoazetidine-1-sulfonate (syn-isomer).

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture is stirred at room temperature for one hour
  3. stirringthe mixture is stirred for 30 minutes
  4. filtrationThe reaction mixture is then filtered
  5. washthe filtrate is washed with ether
  6. customThe aqueous layer is chromatographed on an Amberlite XAD-II column

Sources & evidence

ORD record
ord-c1fb89513cd34fe1a3e53a9a0d52c494
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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