HCID 57195656, compound → HCID 12848997, compound

HRID 610466Notes

Reaction equation

HRID 610466 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[C@@H:7]([CH2:8][C:9](=[O:23])[C:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[N+]=[N-])[NH:6][C:5]1=[O:24])[CH3:3]>C1C=CC=CC=1.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[OH:1][C@@H:2]([C@H:4]1[C:5](=[O:24])[N:6]2[C@@H:7]1[CH2:8][C:9](=[O:23])[CH:10]2[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH3:3]

Participants

4

Reactant 1

HCID 57195656HCID 57195656, compound

Product 1

HCID 12848997HCID 12848997, compound

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 241BenzeneSolvent

Procedure

A suspension of (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-benzyloxycarbonyl-2-oxo-3-diazopropyl] azetidin-2-one (50 mg, 0.15 mmol) and rhodium (II) acetate (0.1 mg) in dry benzene (3 mL) was deoxygenated by bubbling through nitrogen for 10 minutes. The mixture was then heated to 78° for 1 hour. During heating the solid starting material gradually went into solution. The mixture was then cooled, filtered to remove the catalyst, and the filtrate was concentrated in vacuo to yield (5R, 6S) benzyl 6-[(R)-1-hydroxyethyl]-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate, 45 mg. (98%) as a colorless oil.

Workup

  1. customwas deoxygenated
  2. customby bubbling through nitrogen for 10 minutes
  3. temperatureThe mixture was then heated to 78° for 1 hour
  4. temperatureDuring heating the solid
  5. temperatureThe mixture was then cooled
  6. filtrationfiltered
  7. customto remove the catalyst
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-74851815f6624646ba162f5bdd06124d
Source dataset
uspto-grants-1999_12
Patent number
US05998612

Reaction notes

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