Metam-sodium → Sodium 3-[2-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-2-(2-amino-4-thiazolyl)acetamido]-2-oxoazetidine-1-sulfonate

HRID 653237Notes

Reaction equation

HRID 653237 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:38][O:39][CH3:40])[C:12]([NH:14][CH:15]([C:28]2[N:29]=[C:30]([NH:33]C(=O)CCl)[S:31][CH:32]=2)[C:16]([NH:18][CH:19]2[CH2:22][N:21]([S:23]([O-:26])(=[O:25])=[O:24])[C:20]2=[O:27])=[O:17])=[O:13])[N:10]=1)=O.[Na+:41].CNC(=S)[S-].[Na+]>O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:38][O:39][CH3:40])[C:12]([NH:14][CH:15]([C:28]2[N:29]=[C:30]([NH2:33])[S:31][CH:32]=2)[C:16]([NH:18][CH:19]2[CH2:22][N:21]([S:23]([O-:26])(=[O:24])=[O:25])[C:20]2=[O:27])=[O:17])=[O:13])[N:10]=1.[Na+:41]

Participants

4

Reactant 2

HCID 5366415Metam-sodiumHCID 74088530Sodium 3-[2-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-(2-chloroacetamido-4-thiazolyl)acetamido]-2-oxoazetidine-1-sulfonate

Product 1

HCID 74088536Sodium 3-[2-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-2-(2-amino-4-thiazolyl)acetamido]-2-oxoazetidine-1-sulfonateYield 63.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 3 ml of water is dissolved 0.204 g of the above sodium 3-[2-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-(2-chloroacetamido-4-thiazolyl)acetamido]-2-oxoazetidine-1-sulfonate (syn-isomer) and while the solution is stirred under ice-cooling, 0.085 g of sodium N-methyldithiocarbamate is added. The mixture is stirred for an hour, after which the insoluble matter is filtered off. The filtrate is purified by Amberlite XAD-II chromatography to provide 0.1 g of sodium 3-[2-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-2-(2-amino-4-thiazolyl)acetamido]-2-oxoazetidine-1-sulfonate (syn-isomer).

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred for an hour
  3. filtrationafter which the insoluble matter is filtered off
  4. customThe filtrate is purified by Amberlite XAD-II chromatography

Sources & evidence

ORD record
ord-60cfb7e4512c43f996c0513e4306f89d
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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