Acetone → benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

HRID 279772Notes

Reaction equation

HRID 279772 reaction equation
OC1C=CC=C2C=1[NH+]=CC=C2.[O:12]=[C:13]1[C@@H:16]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:15][N:14]1S([O-])(=O)=O.CC(C)=O>C(O)C>[C:22]1([CH2:21][O:20][C:18]([NH:17][C@H:16]2[CH2:15][NH:14][C:13]2=[O:12])=[O:19])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 131714653HCID 131714653, compound

Product 1

HCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A stirred suspension of 1.00 g of (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, 8-hydroxyquinolinium salt in 75 ml of anhydrous ethanol under nitrogen was placed in a 95° C. oil bath. The mixture was refluxed for 20 minutes, then cooled to 20° C. with an ice water bath. The solvent was removed on the rotary evaporator (bath temperature ≥30° C.). The residue was taken up in 10 ml of water and 80 ml of ethyl acetate. About 600 mg of MgSO4 was added followed by 570 mg of sodium bicarbonate. The mixture was stirred to effect solution. The organic layer was separated, washed with 5 ml of water, and dried over MgSO4. The solvent was evaporated to afford a white solid, which was tranferred to a 25 ml flask with acetone. The acetone was removed in vacuo and the solid residue was suspended in ca. 5 ml of ethyl acetate. Ether (ca. 6 ml) was added and the mixture was stored for 60 minutes at 0° C. The solid was isolate by filtration, washed with ether, and dried in vacuo to afford 392 mg of the title compound as a white solid.

Workup

  1. customwas placed in a 95° C.
  2. temperatureThe mixture was refluxed for 20 minutes
  3. customThe solvent was removed on the rotary evaporator (bath temperature ≥30° C.)
  4. additionAbout 600 mg of MgSO4 was added
  5. customThe organic layer was separated
  6. washwashed with 5 ml of water
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated
  9. customto afford a white solid, which
  10. customThe acetone was removed in vacuo
  11. additionEther (ca. 6 ml) was added
  12. customThe solid was isolate by filtration
  13. washwashed with ether
  14. customdried in vacuo

Sources & evidence

ORD record
ord-0428b8ffdf634ab2a06f52962eafd00d
Source dataset
uspto-grants-1986_05
Patent number
US04587051

Reaction notes

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