Putrescine → HCID 57517491, compound

HRID 2368094Notes

Reaction equation

HRID 2368094 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.[F:25]N(S(C1C=CC=CC=1)(=O)=O)S(C1C=CC=CC=1)(=O)=O.[Cl-].[NH4+]>C1COCC1>[F:25][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

6

Reactant 4

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

Product 1

HCID 57517491HCID 57517491, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (2,4-dimethoxyphenyl)carbamate (1.0 g) and tetramethylenediamine (1.4 mL) in THF (10 mL) was added 1.6 M n-butyllithium-hexane solution (7.5 mL) at −78° C., and the mixture was stirred at the same temperature for 20 min and then at 0° C. for 1 hr. To the reaction mixture was added a solution of N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (1.8 g) in THF (10 mL) at −78° C., and the mixture was allowed to warm to room temperature and stirred for 15 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (530 mg).

Workup

  1. waitat 0° C. for 1 hr
  2. stirringstirred for 15 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-165010631012481692c374a101c1fb2d
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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