HCID 86675834, compound → HCID 86675833, compound

HRID 1913539Notes

Reaction equation

HRID 1913539 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:20][C:21]1[N:22]=[CH:23][N:24]([CH:26]2[CH2:31][CH2:30][CH2:29][CH:28]=[CH:27]2)[CH:25]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:20][C:21]1[N:22]=[CH:23][N:24]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:25]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86675834HCID 86675834, compound

Product 1

HCID 86675833HCID 86675833, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

10% palladium-carbon catalyst (hydrated, 200 mg) was suspended in a solution of the compound (250 mg) obtained in Step 1 of this Example in ethanol (6 mL). The suspension was stirred at room temperature for 3 hours under a hydrogen atmosphere at normal pressure. The reaction solution was filtered through celite, and the filtrate was concentrated. The obtained crude product was purified by silica gel column chromatography (eluting solvent: methylene chloride/methanol=20/1−10/1) to obtain the title compound (240 mg).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe obtained crude product
  4. customwas purified by silica gel column chromatography (eluting solvent: methylene chloride/methanol=20/1−10/1)

Sources & evidence

ORD record
ord-4386c3519d4c4e96ad0243478ba65a36
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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