HCID 86714035, compound → HCID 71077020, compound

HRID 2206788Notes

Reaction equation

HRID 2206788 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([CH:11]2[C@H:16]([O:17]CC3C=CC=CC=3)[C@@H:15]([O:25]CC3C=CC=CC=3)[C@H:14]([O:33]CC3C=CC=CC=3)[C@@H:13]([CH2:41][O:42]CC3C=CC=CC=3)[O:12]2)=[CH:4][C:3]=1[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([CH2:57][CH3:58])=[CH:53][CH:52]=1>C1COCC1.CO.[Pd]>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C@H:11]2[C@H:16]([OH:17])[C@@H:15]([OH:25])[C@H:14]([OH:33])[C@@H:13]([CH2:41][OH:42])[O:12]2)=[CH:4][C:3]=1[CH2:50][C:51]1[CH:52]=[CH:53][C:54]([CH2:57][CH3:58])=[CH:55][CH:56]=1

Participants

4

Reactant 1

HCID 86714035HCID 86714035, compound

Product 1

HCID 71077020HCID 71077020, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of compound 35 (1.03 g, 1.30 mmol) in THF/MeOH (30 mL/30 mL) was added Pd/C (10% Pd, 154 mg). The mixture was stirred at rt under hydrogen atmosphere for 15 h. The catalyst removed by filtration, and then the filtrate was concentrated in vacuo. The residue was purified by prep HPLC (reverse phase) to provide the compound E010 (0.28 g, 0.64 mmol, 49%).

Workup

  1. customThe catalyst removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by prep HPLC (reverse phase)
  4. customto provide the compound

Sources & evidence

ORD record
ord-ffa14f515ed04838a60e1cbe018a5af3
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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