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

HRID 653234Notes

Reaction equation

HRID 653234 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:24][O:25][CH3:26])[C:12]([NH:14][CH:15]2[CH2:18][N:17]([S:19]([O-:22])(=[O:21])=[O:20])[C:16]2=[O:23])=[O:13])[N:10]=1)=O.[Na+:27].CNC(=S)[S-].[Na+]>O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:24][O:25][CH3:26])[C:12]([NH:14][CH:15]2[CH2:18][N:17]([S:19]([O-:22])(=[O:20])=[O:21])[C:16]2=[O:23])=[O:13])[N:10]=1.[Na+:27]

Participants

4

Reactant 2

HCID 5366415Metam-sodiumHCID 74088535Sodium 3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-1-sulfonate

Product 1

HCID 74088537Sodium 3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-1-sulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude sodium 3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-1-sulfonate (syn-isomer) obtained above (0.556 g) is dissolved in 8 ml of water, and to the solution is added 0.172 g of sodium N-methyldithiocarbamate under ice-cooling and stirring. The mixture is stirred for 3 hours, after which any insoluble matter is filtered off. The filtrate is purified by XAD-II chromatography to yield 0.174 g of sodium 3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-1-sulfonate (syn-isomer).

Workup

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

Sources & evidence

ORD record
ord-0cd387c396f24ca29e557048d2695bf1
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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