Dimethylformamide → (S)-3-[[(phenylmethyl)carbonyl]amino]-2-azetidinone

HRID 1380804Notes

Reaction equation

HRID 1380804 reaction equation
C1(CO[C:9](=[O:16])[NH:10][C@H:11]2[CH2:14][NH:13][C:12]2=[O:15])C=CC=CC=1.C(N(CC)CC)C.CN(C=O)C.[C:29]1([CH2:35]C(Cl)=O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>[Pd].C(O)C>[O:15]=[C:12]1[C@@H:11]([NH:10][C:9](=[O:16])[CH2:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:14][NH:13]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

Product 1

HCID 13212049(S)-3-[[(phenylmethyl)carbonyl]amino]-2-azetidinoneYield 36.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 5.50 g (0.025 mol) of (S)-(2-oxo-3-azetidinyl) carbamic acid phenylmethyl ester, 250 mL of ethanol, and 2.0 g of 10% palladium on carbon catalyst was hydrogenated (2 hours) on a Parr apparatus at an initial gauge pressure of 50 psi. After filtration of the catalyst, the solution was concentrated to dryness under reduced pressure. A mixture of the residue with 4.2 mL (0.03 mol) of triethylamine and 30 mL of DMF was stirred and cooled in ice. A solution of 3.88 g (0.025 mol) of phenylacetyl chloride in 25 mL of ethanol-free chloroform was added over a period of 30 minutes. The mixture was stirred another 30 minutes with cooling, and then for 2.5 hours at room temperature. The chloroform was evaporated under reduced pressure, and 300 mL of ether was added to the residue. The mixture was cooled in ice for 20 minutes. The precipitate was filtered and washed successively with ether, aqueous NaHCO3 solution, water, and ether. After drying in the air, the solid (2.15 g) was recrystallized from 50 mL of ethanol to obtain 1.86 g of pure (S)-N-(2-oxo-3-azetidinyl)benzeneacetamide, m.p. 194°-195° C.

Workup

  1. custom(2 hours)
  2. filtrationAfter filtration of the catalyst
  3. concentrationthe solution was concentrated to dryness under reduced pressure
  4. temperaturecooled in ice
  5. stirringThe mixture was stirred another 30 minutes
  6. temperaturewith cooling
  7. customThe chloroform was evaporated under reduced pressure, and 300 mL of ether
  8. additionwas added to the residue
  9. temperatureThe mixture was cooled in ice for 20 minutes
  10. filtrationThe precipitate was filtered
  11. washwashed successively with ether, aqueous NaHCO3 solution, water, and ether
  12. customAfter drying in the air
  13. customthe solid (2.15 g) was recrystallized from 50 mL of ethanol

Sources & evidence

ORD record
ord-d7e7bdee9a38426c91f83a38852d8978
Source dataset
uspto-grants-1986_04
Patent number
US04584132

Reaction notes

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