(S)-[1-[[[[4-[[[4,5-Bis(phenylmethoxy)-2-pyridinyl]carbonyl]amino]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester → (S)-N-[4-[[[(3-Amino-2-oxo-1-azetidinyl)carbonyl]amino]sulfonyl]-2,3-dioxo-1-piperazinyl]-1,4-dihydro-5-hydroxy-4-oxo-2-pyridinecarboxamide

HRID 1252623Notes

Reaction equation

HRID 1252623 reaction equation
C1(C[O:8][C:9]2[C:14]([O:15]CC3C=CC=CC=3)=[CH:13][N:12]=[C:11]([C:23]([NH:25][N:26]3[CH2:31][CH2:30][N:29]([S:32]([NH:35][C:36]([N:38]4[CH2:41][C@H:40]([NH:42]C(=O)OCC5C=CC=CC=5)[C:39]4=[O:53])=[O:37])(=[O:34])=[O:33])[C:28](=[O:54])[C:27]3=[O:55])=[O:24])[CH:10]=2)C=CC=CC=1>CN(C)C=O.[Pd]>[NH2:42][C@H:40]1[CH2:41][N:38]([C:36]([NH:35][S:32]([N:29]2[CH2:30][CH2:31][N:26]([NH:25][C:23]([C:11]3[NH:12][CH:13]=[C:14]([OH:15])[C:9](=[O:8])[CH:10]=3)=[O:24])[C:27](=[O:55])[C:28]2=[O:54])(=[O:33])=[O:34])=[O:37])[C:39]1=[O:53]

Participants

4

Reactant 1

HCID 86742167(S)-[1-[[[[4-[[[4,5-Bis(phenylmethoxy)-2-pyridinyl]carbonyl]amino]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

Product 1

HCID 54265560(S)-N-[4-[[[(3-Amino-2-oxo-1-azetidinyl)carbonyl]amino]sulfonyl]-2,3-dioxo-1-piperazinyl]-1,4-dihydro-5-hydroxy-4-oxo-2-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-[1-[[[[4-[[[4,5-bis(phenylmethoxy)-2-pyridinyl]carbonyl]amino]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester (1.54 g, 2 mmol) in 30 ml of dimethylformamide was added 0.77 g of palladium on charcoal, and the mixture was hydrogenolyzed for 45 minutes. The catalyst was removed by filtration over Hyflo and the resulting solution was used for the next step without isolation of the title compound.

Workup

  1. customThe catalyst was removed by filtration over Hyflo

Sources & evidence

ORD record
ord-d39fbfaef0494495bb4860c36372df88
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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