HCID 86741284, compound → HCID 86741286, compound

HRID 235760Notes

Reaction equation

HRID 235760 reaction equation
[N+](=[C:3]([C:17](=[O:29])[CH2:18][C@@H:19]1[C@H:22]([C:23]([O:26][CH3:27])([CH3:25])[CH3:24])[C:21](=[O:28])[NH:20]1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5])=[N-]>C1C=CC=CC=1.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[O:29]=[C:17]1[CH2:18][C@H:19]2[N:20]([C:21](=[O:28])[C@H:22]2[C:23]([O:26][CH3:27])([CH3:24])[CH3:25])[C@H:3]1[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)=[O:5]

Participants

4

Reactant 1

HCID 86741284HCID 86741284, compound

Product 1

HCID 86741286HCID 86741286, compoundYield 103.3%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]-3-oxobutanoate (707 mg) and rhodium (II) acetate (ca. 5 mg) in benzene (20 ml) was refluxed for 30 minutes. After cooling to ambient temperature, the mixture was filtered through cellulose powder. The filtrate was evaporated to give 4-nitrobenzyl (2R,5R,6R)-3,7-dioxo-6-(1-methoxy-1-methylethyl)-1-azabicyclo[3.2.0]heptane-2-carboxylate (680 mg).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. filtrationthe mixture was filtered through cellulose powder
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-362e61b66af14bbc8ed58e1521f0f1ac
Source dataset
uspto-grants-1987_02
Patent number
US04640915

Reaction notes

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