4-nitrobenzyl 2-diazo-4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxo-azetidin-2-yl]-3-oxobutanoate → 4-nitrobenzyl (2R, 5R, 6S)-3,7-dioxo-6-(1-methoxy-1-methylethyl)-1-azabicyclo[3.2.0]-heptane-2-carboxylate

HRID 235752Notes

Reaction equation

HRID 235752 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 867412804-nitrobenzyl 2-diazo-4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxo-azetidin-2-yl]-3-oxobutanoate

Product 1

HCID 867412824-nitrobenzyl (2R, 5R, 6S)-3,7-dioxo-6-(1-methoxy-1-methylethyl)-1-azabicyclo[3.2.0]-heptane-2-carboxylateYield 95.1%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 4-nitrobenzyl 2-diazo-4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxo-azetidin-2-yl]-3-oxobutanoate (56.5 mg) and a catalytic amount of rhodium (II) acetate (ca. 1 mg) in dry benzene (5.6 ml) was refluxed for 30 minutes. After cooling to ambient temperature, the mixture was filtered and evaporated in vacuo to give 4-nitrobenzyl (2R, 5R, 6S)-3,7-dioxo-6-(1-methoxy-1-methylethyl)-1-azabicyclo[3.2.0]-heptane-2-carboxylate (50.0 mg) as an amorphous solid.

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-1b6d123353e2415484d5eb6094393a88
Source dataset
uspto-grants-1987_02
Patent number
US04640915

Reaction notes

Loading…