Ethyl diazoacetate → HCID 66975633, compound

HRID 1022779Notes

Reaction equation

HRID 1022779 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16][OH:17])[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N+](=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N-]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16][O:17][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 66975659HCID 66975659, compound

Product 1

HCID 66975633HCID 66975633, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 1140TolueneSolvent2×

Procedure

Under a nitrogen atmosphere at 80° C., to a solution of tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (600 mg) and rhodium acetate dimer (7 mg) in toluene (5 ml) was added dropwise a solution of ethyl diazoacetate (860 mg) in toluene (5 mL) over 10 min. The reaction mixture was stirred at the same temperature for 10 min. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (615 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0f11b2ac408f4109b3416448f8a0d755
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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