(2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)prop-2-enyl diazoacetate → benzyl 4-[(1S,5R,6R)-2-oxo-3-oxabicyclo[3.1.0]hex-6-yl]phenylcarbamate

HRID 1179487Notes

Reaction equation

HRID 1179487 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7]/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:12][CH:11]=1)=[O:5])=[N-]>ClCCl.C1(C)C=CC=CC=1>[O:5]=[C:4]1[O:6][CH2:7][C@H:8]2[C@@H:3]1[C@@H:9]2[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:18])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 86619689(2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)prop-2-enyl diazoacetate

Product 1

HCID 58978058benzyl 4-[(1S,5R,6R)-2-oxo-3-oxabicyclo[3.1.0]hex-6-yl]phenylcarbamate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)prop-2-enyl diazoacetate (0.7 g, 2.0 mmol) in dichloromethane (20 mL) was added dropwise over 18 h to a refluxing solution of bis-(N-t-butylsalicylaldiminato)copper(II) (0.041 g, 0.01 mmol) in 80 mL of toluene. After the addition was complete, the reaction mixture was heated for another 2 h at reflux and stirred at room temperature for 36 hours. Then the reaction mixture was cooled, filtered and concentrated. The crude oil was purified by silica gel column chromatography (gradient 0-1.5% MeOH-DCM) to provide the title compound and its enantiomer as a racemic mixture.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated for another 2 h
  3. temperatureat reflux
  4. temperatureThen the reaction mixture was cooled
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude oil was purified by silica gel column chromatography (gradient 0-1.5% MeOH-DCM)

Sources & evidence

ORD record
ord-ec5933a9ddca4b10bb6ca4f666d3c4ed
Source dataset
uspto-grants-2007_10
Patent number
US07279494B2

Reaction notes

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