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

HRID 1179477Notes

Reaction equation

HRID 1179477 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][C:11]=1[F:27])=[O:5])=[N-]>C1(C)C=CC=CC=1>[F:27][C:11]1[CH:12]=[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:14]=[CH:15][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

3

Reactant 1

HCID 86600444(2E)-3-(4-{[(benzyloxy)carbonyl]amino}-2-fluorophenyl)prop-2-enyl diazoacetate

Product 1

HCID 11772207benzyl 3-fluoro-4-[(1S,5R,6R)-2-oxo-3-oxabicyclo[3.1.0]hex-6-yl]phenylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of (2E)-3-(4-{[(benzyloxy)carbonyl]amino}-2-fluorophenyl)prop-2-enyl diazoacetate (2.26 g, 6.12 mmol) in toluene (125 mL) was added dropwise over 14 h to a refluxing solution of bis-(N-t-butylsalicylaldiminato)copper(II) (0.254 g, 0.61 mmol, prepared as described by R. G. Charles, J. Org. Chem. 1957, 22, 677) in 125 mL of toluene. After the addition was complete, the reaction mixture was heated another hour at reflux, then cooled, filtered and concentrated. The crude oil was purified by column chromatography (0-0.5% MeOH-DCM) to provide the title compound as a yellow solid.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated another hour
  3. temperatureat reflux
  4. temperaturecooled
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude oil was purified by column chromatography (0-0.5% MeOH-DCM)

Sources & evidence

ORD record
ord-8f7ecf0179784b3b92942c73071acc59
Source dataset
uspto-grants-2007_10
Patent number
US07279494B2

Reaction notes

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