HCID 68838811, compound → HCID 68839446, compound

HRID 2110586Notes

Reaction equation

HRID 2110586 reaction equation
[CH3:1][C:2]1([CH3:28])[O:6][CH:5]([C@H:7]2[N:11]([O:12][CH3:13])[C@:10]3([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[C:14]4[C:19]([C:20](=[O:22])[CH:21]=[C:9]3[O:8]2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:4][O:3]1>C(OCC)(=O)C.O=[Pt]=O>[CH3:1][C:2]1([CH3:28])[O:6][CH:5]([C@H:7]2[N:11]([O:12][CH3:13])[C@:10]3([CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[C:14]4[C:19]([C:20](=[O:22])[CH:21]=[C:9]3[O:8]2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:4][O:3]1

Participants

4

Reactant 1

HCID 68838811HCID 68838811, compound

Product 1

HCID 68839446HCID 68839446, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 22B (82 mg, 0.21 mmol) and PtO2 (Adam's catalyst, 5 mg) in ethyl acetate (2 mL) was stirred at rt under 1 atm H2 for 90 min. The catalyst was filtered off, the solvent was evaporated and the crude product was purified by column chromatography on silica gel using a solvent gradient of 10-25% ethyl acetate in hexanes to provide the title compound as a colorless gum (63 mg, 77%): 1H NMR (300 MHz, DMSO-d6) δ ppm 7.95 (d, J=7.4 Hz, 1H), 7.63-7.79 (m, 2H), 7.42-7.56 (m, 1H), 5.91 (d, J=5.5 Hz, 1H), 5.84 (s, 1H), 4.53-4.67 (m, 1H), 4.09-4.22 (m, 1H), 3.98-4.09 (m, 1H), 3.49 (s, 3H), 1.80-1.97 (m, 2H), 1.45 (s, 3H), 1.36 (s, 3H), 1.21-1.34 (m, 1H), 0.82-1.01 (m, 1H), 0.57-0.74 (m, 6H), 0.32-0.52 (m, 1H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated
  3. customthe crude product was purified by column chromatography on silica gel using a solvent gradient of 10-25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b77476b38cb54f76842eece534638488
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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