HCID 86714057, compound → HCID 71077024, compound

HRID 576424Notes

Reaction equation

HRID 576424 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[C:5]([C@H: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]([O:57][CH2:58][CH3:59])=[CH:53][CH:52]=1>C1COCC1.CO.[Pd]>[Cl:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][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]([O:57][CH2:58][CH3:59])=[CH:55][CH:56]=1

Participants

5

Reactant 1

HCID 86714057HCID 86714057, compound

Product 1

HCID 71077024HCID 71077024, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of compound 81 (2.0 g, 2.46 mmol) and Pd/C (10% wt., 200 mg) in THF (12 mL) and MeOH (12 mL) was stirred at room temperature under an atmosphere of H2 for 16 hours. The mixture was filtered through a Celite pad and concentrated in vacuo. The residue was purified by prep HPLC (C18) to afford the product E024 (514 mg, 46%).

Workup

  1. filtrationThe mixture was filtered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by prep HPLC (C18)
  4. customto afford the product E024 (514 mg, 46%)

Sources & evidence

ORD record
ord-591929ee788f457295ab6309dea7d051
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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