HCID 131726634, compound → HCID 58978060, compound

HRID 1179494Notes

Reaction equation

HRID 1179494 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7]/[CH:8]=[CH:9]/[C:10]1[C:15]([F:16])=[CH:14][C:13]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[CH:12][C:11]=1[F:28])=[O:5])=[N-]>ClCCCl.C1(C)C=CC=CC=1>[F:28][C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:19])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=[C:15]([F:16])[C:10]=1[C@H:9]1[C@H:3]2[C@@H:8]1[CH2:7][O:6][C:4]2=[O:5]

Participants

4

Reactant 1

HCID 131726634HCID 131726634, compound

Product 1

HCID 58978060HCID 58978060, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 1140TolueneSolvent

Procedure

A solution of (2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate (9.7 g, 25.04 mmol) in 100 mL of 1,2-dichloroethane was added dropwise over 14 h to a refluxing solution of bis-(N-t-butylsalicylaldiminato)copper(II) (0.52 g, 1.25 mmol, prepared as described by R. G. Charles, J. Org. Chem. 1957, 22, 677) in toluene (1000 mL). After the addition was complete, the reaction mixture was heated for another hour at reflux, then cooled, filtered and concentrated. The crude oil was purified by column chromatography (0-1% methanol-dichoromethane) to provide the title compound as a racemate.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated for another hour
  3. temperatureat reflux
  4. temperaturecooled
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude oil was purified by column chromatography (0-1% methanol-dichoromethane)

Sources & evidence

ORD record
ord-c689f4c9c30b47d6a40b2f817d2e3c7a
Source dataset
uspto-grants-2007_10
Patent number
US07279494B2

Reaction notes

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