HCID 86714060, compound → HCID 71077032, compound

HRID 576423Notes

Reaction equation

HRID 576423 reaction equation
[Cl:1][C:2]1[C:3]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([CH2:58][CH3:59])=[CH:54][CH:53]=2)=[CH:4][C:5]([CH: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)=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]=[CH:7]2>C1COCC1.CO.[Pd]>[Cl:1][C:2]1[C:3]([CH2:51][C:52]2[CH:53]=[CH:54][C:55]([CH2:58][CH3:59])=[CH:56][CH:57]=2)=[CH:4][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)=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 1

HCID 86714060HCID 86714060, compound

Product 1

HCID 71077032HCID 71077032, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 84 (170 mg, 0.21 mmol) and Pd/C (10 wt. %, 25.5 mg) in THF (2.0 mL) and MeOH (1.0 mL) was stirred at room temperature for 6 hours under atmosphere of H2. The mixture was filtered through a Celite pad and concentrated in vacuo. The residue was purified by a prep HPLC to provide the product E023 (28 mg, 28%) as a white solid.

Workup

  1. filtrationThe mixture was filtered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a prep HPLC
  4. customto provide the product E023 (28 mg, 28%) as a white solid

Sources & evidence

ORD record
ord-6e5ad40a0c6240c7b03945d2b3e587b1
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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