HCID 86740396, compound → HCID 86740395, compound

HRID 653260Notes

Reaction equation

HRID 653260 reaction equation
[C:1]([O:4][C@@H:5]1[N:8]([S:9]([O-:12])(=[O:11])=[O:10])[C:7](=[O:13])[C@H:6]1[NH:14][C:15](=[O:30])[C:16]([C:20]1[N:21]=[C:22]([NH:25]C(=O)CCl)[S:23][CH:24]=1)=[N:17][O:18][CH3:19])(=[O:3])[CH3:2].[Na+:31].CSC(=S)N.[Na]>O>[C:1]([O:4][C@@H:5]1[N:8]([S:9]([O-:12])(=[O:11])=[O:10])[C:7](=[O:13])[C@H:6]1[NH:14][C:15](=[O:30])[C:16]([C:20]1[N:21]=[C:22]([NH2:25])[S:23][CH:24]=1)=[N:17][O:18][CH3:19])(=[O:3])[CH3:2].[Na+:31]

Participants

4

Reactant 2

HCID 86740396HCID 86740396, compoundHCID 86740397HCID 86740397, compound

Product 1

HCID 86740395HCID 86740395, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.101 g of the above sodium (3S,4S)-4-acetoxy-3[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-oxoazetidine-1-sulfonate (syn-isomer) in 4 ml of water is added 28.4 mg of sodium monomethyldithiocarbamate under ice-cooling with stirring, and the mixture is stirred at room temperature for one hour. The insolubles are filtered off and the filtrate is purified on a column of XAD-II. The above procedure gives 55.4 mg of sodium (3S,4S)-4-acetoxy-3[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-oxoazetidine-1-sulfonate (syn-isomer).

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for one hour
  3. filtrationThe insolubles are filtered off
  4. customthe filtrate is purified on a column of XAD-II

Sources & evidence

ORD record
ord-af55af6b86e14da0bc9447b22ab12afd
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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