HCID 86740397, compound → HCID 140340256, compound

HRID 621015Notes

Reaction equation

HRID 621015 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:42]/[O:43][CH3:44])/[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][O:20][C:21](=[O:36])/[C:22](/[C:26]3[N:27]=[C:28]([NH:31]C(=O)CCl)[S:29][CH:30]=3)=[N:23]\[O:24][CH3:25])[N:17]([S:37]([O-:40])(=[O:39])=[O:38])[C:16]2=[O:41])=[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:42]/[O:43][CH3:44])/[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][O:20][C:21](=[O:36])/[C:22](/[C:26]3[N:27]=[C:28]([NH2:31])[S:29][CH:30]=3)=[N:23]\[O:24][CH3:25])[N:17]([S:37]([O-:40])(=[O:39])=[O:38])[C:16]2=[O:41])=[O:13])[N:10]=1.[Na+:45]

Participants

4

Reactant 2

HCID 86740397HCID 86740397, compound2×HCID 140345753HCID 140345753, compound

Product 1

HCID 140340256HCID 140340256, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 221 mg of sodium cis-3-[2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-methoxyiminoacetamido]-4-[2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-methoxyiminoacetoxymethyl]-2-oxoazetidine-1-sulfonate in 10 ml of water is added under ice-cooling 85 mg of sodium monomethyldithiocarbamate with stirring. The mixture is stirred at room temperature for one hour, followed by addition of 40 mg of sodium monomethyldithiocarbamate. The mixture is stirred at room temperature for further one hour. The reaction mixture is washed with ethyl acetate and ether in this order, followed by concentration under reduced pressure. The concentrate is purified by a column chromatography on Amberlite XAD-II, followed by lyophilization to give sodium cis-3-[2-(2-amino-4-thiazolyl)-(Z)-2-methoxyiminoacetamido]-4-[2-(2-amino-4-thiazolyl)-(Z)-2-methoxyiminoacetoxymethyl]-2-oxoazetidine-1-sulfonate.

Workup

  1. stirringThe mixture is stirred at room temperature for one hour
  2. stirringThe mixture is stirred at room temperature for further one hour
  3. washThe reaction mixture is washed with ethyl acetate and ether in this order
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe concentrate is purified by a column chromatography on Amberlite XAD-II

Sources & evidence

ORD record
ord-10ed8c7d1f3a437a88fdb53df5fea7bc
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

Loading…