Putrescine → HCID 57517491, compound

HRID 2277193Notes

Reaction equation

HRID 2277193 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].NCCCCN.CCCCCC.C([Li])CCC.[F:36]N(S(C1C=CC=CC=1)(=O)=O)S(C1C=CC=CC=1)(=O)=O.[Cl-].[NH4+]>C1COCC1>[F:36][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

7

Reactant 5

HCID 1045PutrescineHCID 25517Ammonium ChlorideHCID 588007N-FluorobenzenesulfonimideHCID 10610880Carbamic acid, (2,4-dimethoxyphenyl)-, 1,1-dimethylethyl esterHCID 178418244HCID 178418244, compound

Product 1

HCID 57517491HCID 57517491, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (2,4-dimethoxyphenyl)carbamate (7.09 g) and tetramethylenediamine (12.7 mL) in THF (70 mL) was added 1.6 M n-butyllithium hexane solution (52.5 mL) at −78° C., and the mixture was stirred at the same temperature for 20 min, and then at room temperature for 45 min. To the reaction mixture was added a solution of N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (12.8 g) in THF (30 mL) at −78° C., and the mixture was allowed to warm to room temperature, and stirred overnight. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.90 g).

Workup

  1. waitat room temperature for 45 min
  2. stirringstirred overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-76ceb327c32b4399a9bd0b400086f7d9
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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