HCID 86714049, compound → HCID 71076971, compound

HRID 576421Notes

Reaction equation

HRID 576421 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)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][CH:10]1[C:40]1[C:45]2[CH2:46][CH2:47][O:48][C:44]=2[C:43]([Cl:49])=[C:42]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([CH2:57][CH3:58])=[CH:53][CH:52]=2)[CH:41]=1)C1C=CC=CC=1>C1COCC1.CO.[Pd]>[CH2:57]([C:54]1[CH:53]=[CH:52][C:51]([CH2:50][C:42]2[CH:41]=[C:40]([C@H:10]3[C@H:9]([OH:8])[C@@H:14]([OH:15])[C@H:13]([OH:23])[C@@H:12]([CH2:31][OH:32])[O:11]3)[C:45]3[CH2:46][CH2:47][O:48][C:44]=3[C:43]=2[Cl:49])=[CH:56][CH:55]=1)[CH3:58]

Participants

5

Reactant 1

HCID 86714049HCID 86714049, compound

Product 1

HCID 71076971HCID 71076971, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of compound 72 (490 mg, 0.61 mmol) and Pd/C (10% wt., 74 mg) in THF (4 mL) and MeOH (2 mL) was stirred at room temperature under an atmosphere of H2 for 14 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 E020 (25 mg, 8%) as a brown 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 E020 (25 mg, 8%) as a brown solid

Sources & evidence

ORD record
ord-f1a902f5413d44cfad06735ac09347e6
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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