HCID 57959395, compound → HCID 57959390, compound

HRID 2091450Notes

Reaction equation

HRID 2091450 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H][H]>CO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])(=[O:10])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 57959395HCID 57959395, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 57959390HCID 57959390, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture consisting of crude tert-butyl 2-(3-cyanophenylsulfonamido)-ethylcarbamate (Compound 15, 1.52 g) in methanol (46 mL) under a nitrogen atmosphere was added 5% palladium on carbon (1 g). Hydrogen gas was applied via balloon at atmospheric pressure. The reaction mixture was stirred vigorously for two hours and was subsequently filtered over Celite and rinsed with additional methanol. The mixture was concentrated under reduced pressure and purified by silica chromatography (5:95 methanol-dichloromethane) to afford the title intermediate (650 mg, 42% over two steps).

Workup

  1. filtrationwas subsequently filtered over Celite
  2. washrinsed with additional methanol
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompurified by silica chromatography (5:95 methanol-dichloromethane)

Sources & evidence

ORD record
ord-4bb3aca0084f4d9cb40059e661987591
Source dataset
uspto-grants-2013_05
Patent number
US08440417B2

Reaction notes

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