HCID 86714035, compound → HCID 71077020, compound

HRID 576416Notes

Reaction equation

HRID 576416 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-231e93d2c93746c8af44479d03663baf
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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