HCID 86714091, compound → HCID 71110552, compound

HRID 2206791Notes

Reaction equation

HRID 2206791 reaction equation
[Cl:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[C:5]([C@H:12]2[C@H:17]([O:18]CC3C=CC=CC=3)[C@@H:16]([O:26]CC3C=CC=CC=3)[C@H:15]([O:34]CC3C=CC=CC=3)[C@@H:14]([CH2:42][O:43]CC3C=CC=CC=3)[O:13]2)=[CH:4][C:3]=1[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH3:60])=[CH:54][CH:53]=1>C1COCC1.CO.[Pd]>[Cl:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[C:5]([C@H:12]2[C@H:17]([OH:18])[C@@H:16]([OH:26])[C@H:15]([OH:34])[C@@H:14]([CH2:42][OH:43])[O:13]2)=[CH:4][C:3]=1[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH3:60])=[CH:54][CH:53]=1

Participants

4

Reactant 1

HCID 86714091HCID 86714091, compound

Product 1

HCID 71110552HCID 71110552, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of compound 86 (509 mg, 0.615 mmol) in THF/MeOH (10 mL/10 mL) was added 10% Pd/C (77 mg) at r.t. The reaction mixture was stirred at r.t. for 15 hours under hydrogen and filtered off. The filtrate was concentrated in vacuo and the residue was purified using reverse phase preparative HPLC to provide the title compound E013 (75 mg, 10%).

Workup

  1. filtrationfiltered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified

Sources & evidence

ORD record
ord-14f2c511cd424e25a0b02aaf9248503f
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

Loading…