Ethyl Acetate → 1-{[(3-Phenylpropanoyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic Acid

HRID 1715464Notes

Reaction equation

HRID 1715464 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH2:13][O:14][C:15]([NH:17][C:18]2([C:21]([OH:23])=[O:22])[CH2:20][CH2:19]2)=[O:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC(=O)C)C>[Pd].C(O)C>[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH2:13][O:14][C:15]([NH:17][C:18]2([C:21]([OH:23])=[O:22])[CH2:19][CH2:20]2)=[O:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 247984111-{[((2E)-3-Phenylprop-2-enoyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic Acid

Product 1

HCID 247984941-{[(3-Phenylpropanoyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic AcidYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A dry 100 mL round-bottomed flask equipped with a magnetic stir bar and a rubber septum was charged with 1-{[((2E)-3-phenylprop-2-enoyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic acid (16) (0.8 g, 2.5 mmols) and 10% palladium on carbon in 1:1 mixture of ethylacetate and ethanol. The reaction was done at 1 atm pressure under a hydrogen balloon at room temperature. After the reaction was complete, the solution was filtered through Celite and the solvents removed in vacuo using a rotary evaporator. The dry, crude residue was dissolved in a small amount of a mixture of 60% (v/v) acetonitrile/water (ca. 10 mL), and the solution filtered through a 0.2 μm nylon syringe filter. Final purification was achieved by mass-guided preparative HPLC. After lyophilization of the solvents, 0.646 g (80% yield) of the title compound (17) was obtained as a white solid. M.p: 132.9-134.4° C. 1H NMR (CDCl3, 400 MHz): δ=7.31 (t, 2H), 7.19 (t, 3H), 6.82 (q, 1H), 6.38 (s, 0.3H), 5.50 (s, 0.7H), 2.99 (t, 2H), 2.72 (m, 2H), 1.71 (m, 2H), 1.42 (d, 3H), 1.30 (m, 2H). MS (ESI) m/z 343.93 (M+Na)+, 319.96 (M−H)−.

Workup

  1. customA dry 100 mL round-bottomed flask equipped with a magnetic stir bar
  2. customat room temperature
  3. filtrationthe solution was filtered through Celite
  4. customthe solvents removed in vacuo
  5. customa rotary evaporator
  6. dissolutionThe dry, crude residue was dissolved in a small amount of a mixture of 60% (v/v) acetonitrile/water (ca. 10 mL)
  7. filtrationthe solution filtered through a 0.2 μm nylon syringe
  8. filtrationfilter
  9. customFinal purification

Sources & evidence

ORD record
ord-fca6f7c412a14f71b59ba138cd3b6835
Source dataset
uspto-grants-2010_09
Patent number
US07799829B2

Reaction notes

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