HCID 86740397, compound → HCID 86740433, compound

HRID 978858Notes

Reaction equation

HRID 978858 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:28][O:29][CH2:30][CH3:31])[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+:32].C(=S)(SC)N.[Na]>O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:28][O:29][CH2:30][CH3:31])[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+:32]

Participants

4

Reactant 2

HCID 86740397HCID 86740397, compound2×HCID 86740435HCID 86740435, compound

Product 1

HCID 86740433HCID 86740433, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 110 mg of sodium cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-ethoxyiminoacetamido]-4-methoxycarbonyl-2-oxoazetidine-1-sulfonate (syn-isomer) in 8 ml of water is added under ice-cooling 30 mg of sodium monomethyl dithiocarbamate. The mixture is stirred at room temperature for one hour, then another 10 mg of sodium monomethyl dithiocarbamate is added thereto. After the mixture is stirred for further one hour, the resulting reaction mixture is subjected to filtration, and the filtrate is washed with ether. The aqueous layer is purified by column chromatography on Amberlite XAD-II and then lyophilized to give sodium cis-3-[2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetamido]-4-methoxycarbonyl-2-oxoazetidine-1-sulfonate (syn-isomer).

Workup

  1. stirringAfter the mixture is stirred for further one hour
  2. customthe resulting reaction mixture
  3. filtrationis subjected to filtration
  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-c6d7b4262ab34f7c90d7d9835781a930
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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