HCID 86740397, compound → HCID 86740447, compound

HRID 653277Notes

Reaction equation

HRID 653277 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:28][O:29][CH3:30])[C:12]([NH:14][C@H:15]2[C@H:18]([C:19]([O:21][CH3:22])=[O:20])[N:17]([S:23]([O-:26])(=[O:25])=[O:24])[C:16]2=[O:27])=[O:13])[N:10]=1)=O.[Na+:31].CSC(=S)N.[Na]>O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:28][O:29][CH3:30])[C:12]([NH:14][C@H:15]2[C@H:18]([C:19]([O:21][CH3:22])=[O:20])[N:17]([S:23]([O-:26])(=[O:24])=[O:25])[C:16]2=[O:27])=[O:13])[N:10]=1.[Na+:31]

Participants

4

Reactant 2

HCID 86740397HCID 86740397, compound2×HCID 86740449HCID 86740449, compound

Product 1

HCID 86740447HCID 86740447, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 2 ml of water is dissolved 50 mg of sodium trans-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-methoxycarbonyl-2-oxoazetidine-1-sulfonate (syn-isomer) as obtained in Example 24C, followed by addition of 15 mg of sodium monomethyldithiocarbamate under ice-water cooling and stirring. The mixture is stirred at room temperature for 30 minutes and after further addition of 15 mg of sodium monomethyldithiocarbamate, the mixture is stirred for 30 minutes. The reaction mixture is filtered and the filtrate is washed with ether. The aqueous layer is chromatographed on an Amberlite XAD-II column and lyophilized to give sodium trans-3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-4-methoxycarbonyl-2-oxoazetidine-1-sulfonate (syn-isomer).

Workup

  1. customas obtained in Example 24C
  2. stirringThe mixture is stirred at room temperature for 30 minutes
  3. stirringthe mixture is stirred for 30 minutes
  4. filtrationThe reaction mixture is 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-18f60a74930b4256a6d5ebef00acf5a9
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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