(S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester → (S)-N-[3-[[[(3-Amino-2-oxo-1-azetidinyl)carbonyl]amino]-sulfonyl]tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1,4-dihydro-5-hydroxy-4-oxo-2-pyridinecarboxamide

HRID 2351087Notes

Reaction equation

HRID 2351087 reaction equation
[OH:1][C:2]1[C:3](=[O:40])[CH:4]=[C:5]([C:8]([NH:10][N:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:17]([NH:20][C:21]([N:23]3[CH2:26][C@H:25]([NH:27]C(=O)OCC4C=CC=CC=4)[C:24]3=[O:38])=[O:22])(=[O:19])=[O:18])[C:12]2=[O:39])=[O:9])[NH:6][CH:7]=1>CN(C)C=O.[Pd]>[NH2:27][C@H:25]1[CH2:26][N:23]([C:21]([NH:20][S:17]([N:13]2[CH2:14][CH2:15][CH2:16][N:11]([NH:10][C:8]([C:5]3[NH:6][CH:7]=[C:2]([OH:1])[C:3](=[O:40])[CH:4]=3)=[O:9])[C:12]2=[O:39])(=[O:18])=[O:19])=[O:22])[C:24]1=[O:38]

Participants

4

Reactant 1

HCID 86743424(S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

Product 1

HCID 53731386(S)-N-[3-[[[(3-Amino-2-oxo-1-azetidinyl)carbonyl]amino]-sulfonyl]tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1,4-dihydro-5-hydroxy-4-oxo-2-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

4.95 g (8.57 mmol) (S)-[1-[[[[3-[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester was dissolved in 50 ml N,N-dimethylformamide. After the addition of 2.5 g palladium on carbon, the mixture was hydrogenated for 1 hour. The catalyst was removed and subsequently the filtrate added dropwise to 500 ml isopropanol. The desired product was filtered off, slurried with either and dried in vacuo. Yield 3.03 g, melting range 160°-220° C. (dec.).

Workup

  1. customThe catalyst was removed
  2. additionsubsequently the filtrate added dropwise to 500 ml isopropanol
  3. filtrationThe desired product was filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1506582b737344328de7790582027360
Source dataset
uspto-grants-1989_10
Patent number
US04871841

Reaction notes

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