HCID 86740397, compound → HCID 86740429, compound

HRID 653270Notes

Reaction equation

HRID 653270 reaction equation
CSC(=S)N.[Na].ClCC([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[N:34][O:35][CH3:36])[C:18]([NH:20][C@H:21]2[C@@H:24]([C:25]([O:27][CH3:28])=[O:26])[N:23]([S:29]([O-:32])(=[O:31])=[O:30])[C:22]2=[O:33])=[O:19])[N:16]=1)=O.[Na+:37]>>[NH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[N:34][O:35][CH3:36])[C:18]([NH:20][C@H:21]2[C@@H:24]([C:25]([O:27][CH3:28])=[O:26])[N:23]([S:29]([O-:32])(=[O:30])=[O:31])[C:22]2=[O:33])=[O:19])[N:16]=1.[Na+:37]

Participants

3

Reactant 2

HCID 86740397HCID 86740397, compound2×HCID 86740431HCID 86740431, compound

Product 1

HCID 86740429HCID 86740429, compound

Procedure

Under ice-cooling and stirring, 21 mg of sodium monomethyldithiocarbamate is added to 2 ml of an aqueous solution containing 85 mg of sodium cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-methoxycarbonyl-2-oxoazetidine-1-sulfonate (anti-isomer). The mixture is stirred at room temperature for 1 hour and another 7 mg of sodium monomethyldithiocarbamate is added. The stirring is continued for an additional 1 hour, the reaction mixture is filtered and the filtrate is washed with ether. The aqueous layer is purified by column chromatography on Amberlite XAD-II and the lyophilized to give sodium cis-3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-4-methoxycarbonyl-2-oxoazetidine-1-sulfonate (anti-isomer).

Workup

  1. temperatureUnder ice-cooling
  2. stirringThe mixture is stirred at room temperature for 1 hour
  3. filtrationthe reaction mixture is filtered
  4. washthe filtrate is washed with ether
  5. customThe aqueous layer is purified by column chromatography on Amberlite XAD-II

Sources & evidence

ORD record
ord-752cb43ebfe94dce81cb3a4c085f281e
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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