2-Azetidinone → (S)-3-Amino-N-[(methylamino)sulfonyl]-2-oxo-1-azetidinecarboxamide

HRID 279816Notes

Reaction equation

HRID 279816 reaction equation
[CH3:1][NH:2][S:3]([NH:6][C:7]([N:9]1[CH2:12][C@H:11]([NH:13]C(OCC2C=CC=CC=2)=O)[C:10]1=[O:24])=[O:8])(=[O:5])=[O:4].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[H][H].N1CCC1=O>C(#N)C.[Pd]>[NH2:13][C@H:11]1[CH2:12][N:9]([C:7]([NH:6][S:3]([NH:2][CH3:1])(=[O:5])=[O:4])=[O:8])[C:10]1=[O:24]

Participants

7

Reactant 4

HCID 1367212-AzetidinoneHCID 11708267BistrimethylsilylacetamidHCID 54005555(S)-N-[(Methylamino)sulfonyl]-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinecarboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 54209056(S)-3-Amino-N-[(methylamino)sulfonyl]-2-oxo-1-azetidinecarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent2×

Procedure

(S)-N-[(Methylamino)sulfonyl]-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinecarboxamide (2.1 g; see Example 37) was suspended in 25 ml of acetonitrile and bis(trimethylsilyl)acetamide (3.3 g) was added. The 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. After 15 minutes the catalyst was removed by filtration and 2 ml of methanol was added to the filtrate to precipitate 1.3 g of the title compound.

Workup

  1. customAfter 15 minutes the catalyst was removed by filtration and 2 ml of methanol
  2. additionwas added to the filtrate
  3. customto precipitate 1.3 g of the title compound

Sources & evidence

ORD record
ord-bd09386979e9458aa5f5a4ecf6bb29a4
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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