HCID 68247756, compound → HCID 68247914, compound

HRID 1913546Notes

Reaction equation

HRID 1913546 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11]/[C:12](=[CH:18]\[C:19]1[N:20]=[CH:21][N:22]([CH:24]2[CH2:29][CH2:28][CH2:27][C:26]([CH3:31])([CH3:30])[CH2:25]2)[CH:23]=1)/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:18][C:19]1[N:20]=[CH:21][N:22]([CH:24]2[CH2:29][CH2:28][CH2:27][C:26]([CH3:30])([CH3:31])[CH2:25]2)[CH:23]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 68247756HCID 68247756, compound

Product 1

HCID 68247914HCID 68247914, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

The compound (347 mg) obtained in Step 1 of this Example was dissolved in ethanol (10 mL). To the solution, 10% palladium-carbon catalyst (hydrated, 170 mg) was added, and the mixture was stirred at room temperature for 7 hours under a hydrogen atmosphere. The catalyst was filtered off, and the solvent in the filtrate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-ethyl acetate) to obtain the title compound (337 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationthe solvent in the filtrate was distilled off under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-ethyl acetate)

Sources & evidence

ORD record
ord-591f9e3dec6b458fa9dafb2241e8de70
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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