HCID 86740397, compound → HCID 86740425, compound

HRID 621104Notes

Reaction equation

HRID 621104 reaction equation
CSC(=S)N.[Na].[C:7]([O:10][CH2:11][C@H:12]1[N:15]([S:16]([O-:19])(=[O:18])=[O:17])[C:14](=[O:20])[C@H:13]1[NH:21][C:22](=[O:37])[C:23]([C:27]1[N:28]=[C:29]([NH:32]C(=O)CCl)[S:30][CH:31]=1)=[N:24][O:25][CH3:26])(=[O:9])[CH3:8].[Na+:38]>>[C:7]([O:10][CH2:11][C@H:12]1[N:15]([S:16]([O-:19])(=[O:18])=[O:17])[C:14](=[O:20])[C@H:13]1[NH:21][C:22](=[O:37])[C:23]([C:27]1[N:28]=[C:29]([NH2:32])[S:30][CH:31]=1)=[N:24][O:25][CH3:26])(=[O:9])[CH3:8].[Na+:38]

Participants

3

Reactant 2

HCID 86740397HCID 86740397, compound2×HCID 86740427HCID 86740427, compound

Product 1

HCID 86740425HCID 86740425, compound

Procedure

Under ice-cooling and stirring, 41 mg of sodium monomethyldithiocarbamate is added to 4 ml of an aqueous solution containing 150 mg of sodium cis-4-acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-1-sulfonate (syn-isomer). The mixture is stirred at room temperature for 30 minutes, and another 10 mg of sodium monomethyldithiocarbamate is added. The stirring is continued for an additional 30 minutes, and the reaction mixture is filtered. The filtrate is then washed with ether, and the aqueous layer is purified by column chromatography on Amberlite XAD-II and then lyophilized to give sodium cis-4-acetoxymethyl-3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-1-sulfonate (syn-isomer).

Workup

  1. temperatureUnder ice-cooling
  2. stirringThe mixture is stirred at room temperature for 30 minutes
  3. filtrationthe reaction mixture is filtered
  4. washThe filtrate is then washed with ether
  5. customthe aqueous layer is purified by column chromatography on Amberlite XAD-II

Sources & evidence

ORD record
ord-77a4c18dd0e145fbb578d47e44632f7d
Source dataset
uspto-grants-1989_04
Patent number
US04822788

Reaction notes

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