Bistrimethylsilylacetamid → HCID 14390891, compound

HRID 2292333Notes

Reaction equation

HRID 2292333 reaction equation
C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[OH:13][C:14]1[CH:15]=[C:16]([CH:43]=[CH:44][C:45]=1[OH:46])[C:17]([NH:19][NH:20][S:21]([NH:24][C:25]([N:27]1[CH2:30][C@H:29]([NH:31]C(=O)OCC2C=CC=CC=2)[C:28]1=[O:42])=[O:26])(=[O:23])=[O:22])=[O:18].[H][H]>C(#N)C.[Pd]>[NH2:31][C@H:29]1[CH2:30][N:27]([C:25]([NH:24][S:21]([NH:20][NH:19][C:17](=[O:18])[C:16]2[CH:43]=[CH:44][C:45]([OH:46])=[C:14]([OH:13])[CH:15]=2)(=[O:22])=[O:23])=[O:26])[C:28]1=[O:42]

Participants

6

Reactant 3

HCID 11708267BistrimethylsilylacetamidHCID 86742701HCID 86742701, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14390891HCID 14390891, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

7.4 ml of bis(trimethylsilyl)acetamide (0.03 mol) was added to a suspension of 2.47 g (0.005 mol) of (S)-[1-[[[[2-(3,4-dihydroxybenzoyl)hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester (see Example 3A) in 40 ml of acetonitrile. After stirring for 15 minutes, a clear solution was obtained. One gram of palladium on charcoal (10%) was added and hydrogen was passed through the solution with stirring. The catalyst was filtered off and 2 ml of methanol were added to the solution, followed by a few drops of acetic acid. The mixture was stirred for 2 hours with cooling (ice/water) and the precipitate was filtered off, washed with acetonitrile and petroleum ether to yield 1.5 g of (S)-3-amino-N-[[2-(3,4-dihydroxybenzoyl)hydrazino]sulfonyl]-2-oxo-1-azetidinecarboxamide.

Workup

  1. customa clear solution was obtained
  2. stirringwith stirring
  3. filtrationThe catalyst was filtered off
  4. addition2 ml of methanol were added to the solution
  5. stirringThe mixture was stirred for 2 hours
  6. temperaturewith cooling (ice/water)
  7. filtrationthe precipitate was filtered off
  8. washwashed with acetonitrile and petroleum ether

Sources & evidence

ORD record
ord-376b7e99de4d480084c5358f6a83eb2a
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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