HCID 20823149, compound → HCID 20823157, compound

HRID 1393506Notes

Reaction equation

HRID 1393506 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[C:5]([CH3:32])([O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][CH:26]=[CH:25]2)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:33])[C:5]([CH3:32])([O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][CH:26]=[CH:25]2)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 20823149HCID 20823149, compound

Product 1

HCID 20823157HCID 20823157, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(4-Benzyloxy-phenyl)-2-methyl-2-(quinolin-6-yloxy)-propionic acid ethyl ester (2.65 g, 6.0 mmol) in 100 mL of EtOH with 5% Pd/C (530 mg, 20 w %) was allowed to stand under 1 atm H2 for 6 h. Catalyst was filtered off and organic solvent was removed under vacuum. Residue was then dissolved in 200 mL of toluene. 530 mg of 10% Pd/C was added. The mixture was heated to reflux under air for overnight. Reaction was cooled to r.t. and catalyst was filtered off. Organic solvent was removed under vacuum and crude material was clean for next step without further purification. 1H NMR (400 MHz, CDCl3) δδ8.77 (dd, 1H, J=4.0, 1.4 Hz), 8.04 (d, 1H, J=7.6 Hz), 8.02 (d, 1H, J=9.6 Hz), 7.38 (dd, 1H, J=8.4, 4.4 Hz), 7.32 (dd, 1H, J=9.2, 2.8 Hz), 7.09 (d, 2H, J=8.8 Hz), 7.03 (d, 1H, J=2.8 Hz), 6.83 (d, 2H, J=8.8 Hz), 4.22 (q, 2H, J=7.1 Hz), 3.35, 3.13 (ABq, 2H, J=13.6 Hz), 1.52 (s, 3H), 1.19 (t, 3H, J=7.1 Hz). MS (ES+) m/z mass calcd for C21H22NO4 (m+1) 352, found 352.

Workup

  1. filtrationCatalyst was filtered off
  2. customorganic solvent was removed under vacuum
  3. dissolutionResidue was then dissolved in 200 mL of toluene
  4. addition530 mg of 10% Pd/C was added
  5. temperatureThe mixture was heated
  6. temperatureto reflux under air for overnight
  7. customReaction
  8. filtrationcatalyst was filtered off
  9. customOrganic solvent was removed under vacuum and crude material
  10. customwas clean for next step without further purification

Sources & evidence

ORD record
ord-a423576a63db4d7cae6d2e1a9d99cf99
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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