Trifluoroacetic acid → HCID 131715532, compound

HRID 1252637Notes

Reaction equation

HRID 1252637 reaction equation
[CH3:1][N:2]([C:26]([C:28]1[N:29](CC2C=CC=CC=2)[CH:30]=[C:31]([O:35]CC2C=CC=CC=2)[C:32](=[O:34])[CH:33]=1)=[O:27])[NH:3][S:4]([NH:7][C:8]([N:10]1[CH2:13][C@H:12]([NH:14]C(OCC2C=CC=CC=2)=O)[C:11]1=[O:25])=[O:9])(=[O:6])=[O:5].[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53]>CN(C)C=O.[Pd]>[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].[NH2:14][CH:12]1[CH2:13][N:10]([C:8]([NH:7][S:4]([NH:3][N:2]([CH3:1])[C:26]([C:28]2[NH:29][CH:30]=[C:31]([OH:35])[C:32](=[O:34])[CH:33]=2)=[O:27])(=[O:5])=[O:6])=[O:9])[C:11]1=[O:25]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131715534HCID 131715534, compound

Product 1

HCID 131715532HCID 131715532, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 g of (S)-1,4-dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinecarboxylic acid, 1-methyl-2-[[[[2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinyl]carbonyl]amino]sulfonyl]hydrazide in 60 ml of dimethylformamide, 1.1 ml of trifluoroacetic acid was added, followed by one gram of palladium on charcoal (10%). After flushing with nitrogen, hydrogen was passed through the solution for 60 minutes with stirring, the catalyst was removed by filtration, the filtrate evaporated in vacuo and the residue triturated with ether to yield 1.1 g of crude title compound. Yield: 86.6%.

Workup

  1. customAfter flushing with nitrogen, hydrogen
  2. customthe catalyst was removed by filtration
  3. customthe filtrate evaporated in vacuo
  4. customthe residue triturated with ether

Sources & evidence

ORD record
ord-f685b2dc0fe642ffa40c0478d278e646
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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