HCID 89601144, compound → HCID 89602217, compound

HRID 530246Notes

Reaction equation

HRID 530246 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([C:13]3[C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]([CH3:22])([CH3:21])[CH:14]=3)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1>C(O)(=O)C.[Pt](=O)=O>[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([C:13]3[C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]([CH3:22])([CH3:21])[CH:14]=3)=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

4

Reactant 1

HCID 89601144HCID 89601144, compound

Product 1

HCID 89602217HCID 89602217, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To the product of Example 10i (130 mg, 0.47 mmol) in acetic acid (2 mL) was added platinum dioxide (20 mg) and the reaction mixture was stirred under an atmosphere of hydrogen for 3 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with saturated aqueous sodium bicarbonate and the aqueous layer was extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the title compound (59 mg, Yield: 42%). 1H NMR (400 MHz, CDCl3) δ 7.50 (s, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.06 (d, J=8.0 Hz, 1H), 5.77 (s, 1H), 4.11 (s, 2H), 3.21 (t, J=5.6 Hz, 2H), 2.90 (t, J=5.6 Hz, 2H), 2.32 (s, 1H), 1.58 (s, 4H), 1.24 (s, 6H), 1.05 (s, 6H) ppm.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with saturated aqueous sodium bicarbonate
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0141ae6bda304bbca4cefebdb4f64a77
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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