HCID 66931171, compound → HCID 44128632, compound

HRID 512008Notes

Reaction equation

HRID 512008 reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][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]([CH2:27][O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:25][N:26]=2)=[O:21])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH2:29]([O:28][CH2:27][C:24]1[O:23][C:22]([C:20](=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:13][C:12]2[CH:36]=[CH:37][C:9]([OH:8])=[CH:10][CH:11]=2)=[N:26][N:25]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 1

HCID 66931171HCID 66931171, compound

Product 1

HCID 44128632HCID 44128632, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 73.2 (50 mg, 0.1 mmol) and Pd/C (10 mg) in AcOEt (5 mL) was stirred vigorously under hydrogen overnight at room temperature. The catalyst was removed by filtration through celite and the filtrate was evaporated under reduced pressure. The crude material was purified through a column of silica gel, eluting with 45% ethyl acetate-petroleum ether to give 74.2 as a white solid in 75% yield (31 mg).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe crude material was purified through a column of silica gel
  4. washeluting with 45% ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-23330bc2b2da4984913d49024d71aea7
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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