HCID 56613986, compound → HCID 86741068, compound

HRID 2290420Notes

Reaction equation

HRID 2290420 reaction equation
[C:1]([NH:9][C@@H:10]1[C@@H:13]([O:14][CH2:15][C:16](=[O:27])[C:17](=[N+]=[N-])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[NH:12][C:11]1=[O:28])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1C=CC=CC=1.O1CCCC1.[Hg]>[C:1]([NH:9][C@H:10]1[C:11](=[O:28])[N:12]2[C@@H:13]1[O:14][CH2:15][C:16]([OH:27])=[C:17]2[C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 56613986HCID 56613986, compound

Product 1

HCID 86741068HCID 86741068, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 22633675Benzene tetrahydrofuranSolvent

Procedure

An anhydrous and degassed solution of 78 mg (0.2 mmol) of tert.-butyl 4-[3(R)-benzoylamino-2-azetidinon-4-(R)-yloxy]-2-diazo-3-oxo-butyrate in 25 ml of benzene:tetrahydrofuran 3:1 was irradiated in a nitrogen atmosphere at 20° C. for 1 hour with a 450 W mercury vapour lamp with a Pyrex filter. The solvent was evaporated off in vacuo and the residue was purified by chromatography on 8 g of silica gel (toluene:ethyl acetate 35:65). 12 mg (17%) of the title compound were obtained as a colorless rigid foam.

Workup

  1. filtrationfilter
  2. customThe solvent was evaporated off in vacuo
  3. customthe residue was purified by chromatography on 8 g of silica gel (toluene:ethyl acetate 35:65)

Sources & evidence

ORD record
ord-0c6ebf9152184cc3b90ca36e34ed5ba2
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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