HCID 137329129, compound → HCID 131715977, compound

HRID 1905099Notes

Reaction equation

HRID 1905099 reaction equation
[C:1]([C@@H:5]([C@H:11]1[C@@H:14]([CH2:15][C:16](=[O:26])[C:17]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])=[N+]=[N-])[NH:13][C:12]1=[O:27])[CH2:6][O:7][SiH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]>ClCCl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[CH2:23]([O:22][C:20]([C@@H:17]1[C:16](=[O:26])[CH2:15][C@H:14]2[N:13]1[C:12](=[O:27])[C@H:11]2[C@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][O:7][SiH:8]([CH3:10])[CH3:9])=[O:21])[CH:24]=[CH2:25]

Participants

4

Reactant 1

HCID 137329129HCID 137329129, compound

Product 1

HCID 131715977HCID 131715977, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.96 g (10 mmol) of (3S,4R)-3-[(1R)-1-tert.-butyldimethylsilyloxyethyl]-4-[3-allyloxycarbonyl-3-diazo-2-oxopropyl]azetidin-2-one in 50 ml of anhydrous dichloromethane was heated to reflux for 30 minutes in the presence of 40 mg (1 mol-%) of rhodium(II) acetate. The reaction solution was filtered through a little kieselguhr and silica gel and evaporated in vacuo. 3.5 g (95%) of the title compound were obtained as a colorless oil, Rf: 0.46 (toluene:ethyl acetate 7:3).

Workup

  1. filtrationThe reaction solution was filtered through a little kieselguhr and silica gel
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-b7d6ddb69a15428da6661f5b2fec6392
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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