HCID 86714090, compound → HCID 71078265, compound

HRID 2206787Notes

Reaction equation

HRID 2206787 reaction equation
C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[CH:12]([C:31]2[CH:39]=[C:38]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=3)[C:37]([Cl:49])=[C:36]3[C:32]=2[CH2:33][CH2:34][CH2:35]3)[O:11][C@@H:10]1[CH2:50][O:51]CC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.CO.[Pd]>[Cl:49][C:37]1[C:38]([CH2:40][C:41]2[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)=[CH:39][C:31]([C@H:12]2[C@H:13]([OH:23])[C@@H:14]([OH:15])[C@H:9]([OH:8])[C@@H:10]([CH2:50][OH:51])[O:11]2)=[C:32]2[C:36]=1[CH2:35][CH2:34][CH2:33]2

Participants

4

Reactant 1

HCID 86714090HCID 86714090, compound

Product 1

HCID 71078265HCID 71078265, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of compound 18 (0.87 g, 1.09 mmol) in THF/MeOH (8.9 mL/8.9 mL) were added Pd/C (10% Pd, 122 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 E005 (0.11 g, 0.25 mmol, 23%).

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-f2f88731d9ac4bd19ff3d3a5e180c149
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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