Acetic Acid → HCID 23705535, compound

HRID 465183Notes

Reaction equation

HRID 465183 reaction equation
[C:1]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([NH:22][CH:23]1[CH2:26][N:25]([S:27]([O-:30])(=[O:29])=[O:28])[C:24]1=[O:31])=[O:21])(OCC1C=CC=CC=1)=[O:2].[Na+:32].[C:33]([OH:36])(=O)C>CO.[H][H].[Pd]>[O:36]=[C:33]1[NH:25][CH2:24][CH2:23][N:22]1[C:1]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([NH:22][CH:23]1[CH2:26][N:25]([S:27]([O-:30])(=[O:29])=[O:28])[C:24]1=[O:31])=[O:21])=[O:2].[Na+:32]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 23705552HCID 23705552, compound

Product 1

HCID 23705535HCID 23705535, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

In 70 ml of 30% methanol is dissolved 0.30 g of the sodium 3-[2-(2-carbobenzoxyaminomethylphenyl)acetamido]-2-oxoazetidine-1-sulfonate obtained in Example 80 followed by addition of 0.68 ml of 6% acetic acid and 75 mg of palladium black. The mixture is stirred in hydrogen gas streams at room temperature for 90 minutes, after which the catalyst is filtered off. The filtrate is concentrated under reduced pressure, followed by ddition of 30 ml of tetrahydrofuran. Then, under ice-cooling, 0.15 g of 1-chlorocarbonylimidazolid-2-one is added to the above tetrahydrofuran solution. The mixture is stirred for 90 minutes (its pH being maintained at 8.5 with a 1% aqueous solution of sodium hydrogen carbonate). The reaction mixture is adjusted to pH 6.5 with phosphoric acid, and the tetrahydrofuran is distilled off under reduced pressure. The residue is purified on an Amberlite XAD-II column to provide 0.24 g of sodium 3-[2-[2-(2-oxoimidazolidin-1 -yl)carbonylaminomethylphenyl]acetamido]-2-oxoazetidine-1-sulfonate.

Workup

  1. filtrationafter which the catalyst is filtered off
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. temperatureThen, under ice-cooling
  4. addition0.15 g of 1-chlorocarbonylimidazolid-2-one is added to the above tetrahydrofuran solution
  5. temperaturebeing maintained at 8.5 with a 1% aqueous solution of sodium hydrogen carbonate)
  6. distillationthe tetrahydrofuran is distilled off under reduced pressure
  7. customThe residue is purified on an Amberlite XAD-II column

Sources & evidence

ORD record
ord-e8a44902d7784a31afcd78c7538f394b
Source dataset
uspto-grants-1985_10
Patent number
US04550105

Reaction notes

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