(e)-(6r,7r)-7-(2-Bromo-acetylamino)-3-(1-cyclopropyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt → (e)-(6r,7r)-7-[2-(1h-Benzoimidazol-2-ylsulfanyl)-acetylamino]-3-(1-cyclopropyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt

HRID 1597707Notes

Reaction equation

HRID 1597707 reaction equation
[Na+:1].Br[CH2:3][C:4]([NH:6][C@@H:7]1[C:14](=[O:15])[N:13]2[C@@H:8]1[S:9][CH2:10][C:11](/[CH:19]=[C:20]1/[C:21](=[O:28])[N:22]([CH:25]3[CH2:27][CH2:26]3)[CH2:23][CH2:24]/1)=[C:12]2[C:16]([O-:18])=[O:17])=[O:5].[Na].[SH:30][C:31]1[NH:32][C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=1>CN(C)C=O>[Na+:1].[NH:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=[C:31]1[S:30][CH2:3][C:4]([NH:6][C@@H:7]1[C:14](=[O:15])[N:13]2[C@@H:8]1[S:9][CH2:10][C:11](/[CH:19]=[C:20]1/[C:21](=[O:28])[N:22]([CH:25]3[CH2:27][CH2:26]3)[CH2:23][CH2:24]/1)=[C:12]2[C:16]([O-:18])=[O:17])=[O:5]

Participants

4

Reactant 2

HCID 69467792(e)-(6r,7r)-7-(2-Bromo-acetylamino)-3-(1-cyclopropyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium saltHCID 178527776HCID 178527776, compound

Product 1

HCID 69468622(e)-(6r,7r)-7-[2-(1h-Benzoimidazol-2-ylsulfanyl)-acetylamino]-3-(1-cyclopropyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-(6R,7R)-7-(2-bromo-acetylamino)-3-(1-cyclopropyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt (1:1) (see ex. C4a) (200 mg, 0.42 mmol) was dissolved in 4 ml N,N-dimethylformamide and 2-mercaptobenzimidazole sodium salt (79.2 mg, 0.46 mmol) was added in a single portion. After completion of the reaction, the solvent was stripped off at a rotary evaporator. The residue was dissolved in water and chromatographed on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitril (10:1, 9:1). The organic solvent was evaporated and the aqueous phase was freeze-dried.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was stripped off at a rotary evaporator
  3. dissolutionThe residue was dissolved in water
  4. customchromatographed on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitril (10:1, 9:1)
  5. customThe organic solvent was evaporated
  6. customthe aqueous phase was freeze-dried

Sources & evidence

ORD record
ord-c768102d924340209eefc68c17a9b7a6
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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