HCID 66849998, compound → HCID 66849895, compound

HRID 910718Notes

Reaction equation

HRID 910718 reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH:4]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17]C(OCC2C=CC=CC=2)=O)=[CH:9][CH:8]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:36])[CH:4]([NH:28][C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 66849998HCID 66849998, compound

Product 1

HCID 66849895HCID 66849895, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 15 (505 mg, 1.00 mmol) was dissolved in methanol (20 mL) and 10% palladium on carbon (100 mg) was added. The flask was evacuated, filled with hydrogen gas under balloon pressure and stirred overnight. Filtration through celite to remove the catalyst followed by removal of the solvent under reduced pressure provided compound 16 (366 mg, 98%). 1H NMR (300 MHz, CDCl3) δ 7.08 (d, 2H), 6.80 (d, 2H), 5.51 (d, 1H), 4.66 (m, 1H), 4.38 (m, 1H), 4.17 (m, 1H), 3.78 (s, 3H), 2.73 (m, 2H), 2.58 (m, 2H), 1.90 (br s, 2H), 1.62 (m, 2H), 1.50 (m, 2H), 1.48 (s, 9H).

Workup

  1. customThe flask was evacuated
  2. additionfilled with hydrogen gas under balloon pressure
  3. filtrationFiltration through celite
  4. customto remove the catalyst
  5. customfollowed by removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1a4e5ef05e0a4e0789690324fb292879
Source dataset
uspto-grants-2011_09
Patent number
US08022210B2

Reaction notes

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