HCID 86740397, compound → HCID 86740458, compound

HRID 621114Notes

Reaction equation

HRID 621114 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:27][O:28][C:29]([CH3:44])([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=2)=[O:32])[CH3:30])[C:12]([NH:14][C@H:15]2[C@@H:18]([C:19](=[O:21])[NH2:20])[N:17]([S:22]([O-:25])(=[O:24])=[O:23])[C:16]2=[O:26])=[O:13])[N:10]=1)=O.[Na+:45].CSC(=S)N.[Na]>O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:27][O:28][C:29]([CH3:44])([C:31]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=2)=[O:32])[CH3:30])[C:12]([NH:14][C@H:15]2[C@@H:18]([C:19](=[O:21])[NH2:20])[N:17]([S:22]([O-:25])(=[O:24])=[O:23])[C:16]2=[O:26])=[O:13])[N:10]=1.[Na+:45]

Participants

4

Reactant 2

HCID 86740397HCID 86740397, compoundHCID 86741505HCID 86741505, compound

Product 1

HCID 86740458HCID 86740458, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 20 ml of water is dissolved 280 mg of sodium cis-3-{2-(2-chloroacetamido-4-thiazolyl)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetamido}-4-carbamoyl-2-oxoazetidine-1-sulfonate (syn-isomer) as obtained in Example 131C, and under ice-cooling and stirring, 104 mg of sodium monomethyldithiocarbamate is added. The mixture is stirred at room temperature for 1.5 hours. The reaction mixture is twice washed with ether, and then purified by column chromatography on Amberlite XAD-II (40 g), eluting with water and then 20% ethanol. The fractions including the desired product are combined and lyophilized to give sodium cis-3-{2-(2-amino-4-thiazolyl)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetamido}-4-carbamoyl-2-oxoazetidine-1-sulfonate (syn-isomer).

Workup

  1. customas obtained in Example 131C
  2. temperatureunder ice-cooling
  3. stirringThe mixture is stirred at room temperature for 1.5 hours
  4. washThe reaction mixture is twice washed with ether
  5. custompurified by column chromatography on Amberlite XAD-II (40 g)
  6. washeluting with water

Sources & evidence

ORD record
ord-a3413cda99a64d61a1f666d150894aec
Source dataset
uspto-grants-1989_04
Patent number
US04822788

Reaction notes

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