2-Azetidinone → HCID 54244271, compound

HRID 279817Notes

Reaction equation

HRID 279817 reaction equation
[O:1]=[C:2]1[C@@H:5]([NH:6]C(OCC2C=CC=CC=2)=O)[CH2:4][N:3]1[C:17]([NH:19][S:20]([NH:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)(=[O:22])=[O:21])=[O:18].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[H][H].N1CCC1=O>C(#N)C.[Pd]>[NH2:6][C@H:5]1[CH2:4][N:3]([C:17]([NH:19][S:20]([NH:23][C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)(=[O:22])=[O:21])=[O:18])[C:2]1=[O:1]

Participants

7

Reactant 4

HCID 1367212-AzetidinoneHCID 11708267BistrimethylsilylacetamidHCID 53832470HCID 53832470, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54244271HCID 54244271, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent2×

Procedure

(S)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-N-[[(4-pyridyl)amino]sulfonyl]-1-azetidinecarboxamide (2.1 g; see example 36) was suspended in 25 ml of acetonitrile and 3 g (3.6 ml) of bis(trimethylsilyl)acetamide was added with stirring. After a few minutes a clear solution was formed. This solution was added to a suspension of 1 g of 10% palladium on charcoal in 25 ml of acetonitrile, through which hydrogen was passed for 30 minutes prior to the addition of the solution of the starting azetidinone. Hydrogenation was complete after 70 minutes. The catalyst was removed by filtration. On addition of 1 ml of methanol the title compound crystallized from the solution; yield 1.0 g.

Workup

  1. customAfter a few minutes a clear solution was formed
  2. waitHydrogenation was complete after 70 minutes
  3. customThe catalyst was removed by filtration
  4. additionOn addition of 1 ml of methanol the title compound
  5. customcrystallized from the solution

Sources & evidence

ORD record
ord-9dd5b7143d9d477faf3c61ac2927607f
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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