HCID 67237164, compound → HCID 67236605, compound

HRID 1470953Notes

Reaction equation

HRID 1470953 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[C@@H:19]([O:20][CH3:21])[C@H:18]([O:22][CH3:23])[C@H:17]([C:24]3[CH:29]=[CH:28][C:27]([O:30]CC4C=CC=CC=4)=[CH:26][CH:25]=3)[N:16]2[C:38]2[CH:43]=[CH:42][C:41]([C:44]([CH3:47])([CH3:46])[CH3:45])=[CH:40][CH:39]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:44]([C:41]1[CH:40]=[CH:39][C:38]([N:16]2[C@@H:17]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[C@@H:18]([O:22][CH3:23])[C@H:19]([O:20][CH3:21])[C@@H:15]2[C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[CH:43][CH:42]=1)([CH3:47])([CH3:45])[CH3:46]

Participants

4

Reactant 1

HCID 67237164HCID 67237164, compound

Product 1

HCID 67236605HCID 67236605, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Example 48B (168 mg, 0.268 mmol) in ethyl acetate (3 ml) was added 10% palladium on carbon (17 mg) and the flask was evacuated and back-filled with H2 gas. The solution was stirred under a balloon of H2 gas for 20 h, filtered through Celite, and washed with ethyl acetate and methanol. The filtrate was concentrated and the residue was azeotroped with ether to give title compound (120 mg, 100%) as a white solid.

Workup

  1. customthe flask was evacuated
  2. additionback-filled with H2 gas
  3. filtrationfiltered through Celite
  4. washwashed with ethyl acetate and methanol
  5. concentrationThe filtrate was concentrated
  6. customthe residue was azeotroped with ether

Sources & evidence

ORD record
ord-62f2202c2b09451791ab317b982bd995
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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