HCID 131714653, compound → benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

HRID 279768Notes

Reaction equation

HRID 279768 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>C(#N)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

3

Reactant 1

HCID 131714653HCID 131714653, compound

Product 1

HCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3S)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, 8-hydroxyquinolinium salt (150 mg, 0.337 mmol) was added to acetonitrile (10 ml) and rapidly heated to reflux in a preheated oil bath. After refluxing for a total of 18 minutes, the mixture was cooled to room temperature, filtered through Celite, and solvent was removed in vacuo. The residue was extracted with an acetonitrile-ethyl acetate mixture and the extract chromatographed on a silica gel column (Mallinckrodt SilicAR CC-7). The desired product (31 mg) was eluted with a 5% acetonitrile:95% ethyl acetate mixture.

Workup

  1. temperaturerapidly heated
  2. temperatureto reflux in a preheated oil bath
  3. temperatureAfter refluxing for a total of 18 minutes
  4. filtrationfiltered through Celite, and solvent
  5. customwas removed in vacuo
  6. extractionThe residue was extracted with an acetonitrile-ethyl acetate mixture
  7. customthe extract chromatographed on a silica gel column (Mallinckrodt SilicAR CC-7)
  8. washThe desired product (31 mg) was eluted with a 5% acetonitrile

Sources & evidence

ORD record
ord-f428fde5c4ef4ccca9b1a16a79e8f0b1
Source dataset
uspto-grants-1986_05
Patent number
US04587051

Reaction notes

Loading…