HCID 25018605, compound → HCID 25018606, compound

HRID 512002Notes

Reaction equation

HRID 512002 reaction equation
C([O:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([C:22]2[O:23][C:24]([CH3:27])=[N:25][N:26]=2)=[O:21])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([C:22]2[O:23][C:24]([CH3:27])=[N:25][N:26]=2)=[O:21])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 25018605HCID 25018605, compound

Product 1

HCID 25018606HCID 25018606, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 65.2 (30 mg, 0.076 mmol) in AcOEt (5 mL) was added 10% Pd/C (6 mg, 20% w/w) and the resulting suspension was stirred vigorously under hydrogen atmosphere, overnight at room temperature. The catalyst was removed by filtration through Celite, and the filtrate was evaporated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (60% ethyl acetate-hexane) to give pure compound 66 (0.016 g, 71% yield) as a white solid (m p 134-135° C.).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue obtained
  4. customwas purified by flash column chromatography on silica gel (60% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-216604b4c7544d25adcddb5f985159ae
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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