HCID 86714047, compound → HCID 71077007, compound

HRID 576420Notes

Reaction equation

HRID 576420 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][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]([O:57][CH3:58])=[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][CH3:58])=[CH:55][CH:56]=1

Participants

5

Reactant 1

HCID 86714047HCID 86714047, compound

Product 1

HCID 71077007HCID 71077007, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of compound 68 (340 mg, 0.48 mmol) and Pd/C (10% wt., 45 mg) in THF (4.0 mL) and MeOH (2.0 mL) was stirred at room temperature under an atmosphere of H2 for 24 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 E019 (15 mg, 7%) as a white solid.

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 E019 (15 mg, 7%) as a white solid

Sources & evidence

ORD record
ord-3bba410d78224e31b770c37487a4443a
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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