Sodium hydride → HCID 86675820, compound

HRID 1913512Notes

Reaction equation

HRID 1913512 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].[Cl-].[NH4+]>O1CCCC1>[C:26]([O:25][C:24]([NH:23][CH2:22][CH2:21][CH2:20][CH:9]([P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[O:30])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 86675820HCID 86675820, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

tert-Butyl diethylphosphonoacetate (20.0 g) was dissolved in tetrahydrofuran (500 mL). To the solution, sodium hydride (63%, 3.32 g) was added at 0° C., and the mixture was stirred at 0° C. for 15 minutes and at room temperature for 1 hour. A solution of tert-butyl (3-bromopropyl)carbamate (20.0 g) in tetrahydrofuran (20 mL) was slowly added thereto at room temperature, and the mixture was stirred at room temperature for 18 hours. To the reaction solution, saturated aqueous ammonium chloride was added, and organic matter was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-ethyl acetate) to obtain the title compound (26.6 g).

Workup

  1. stirringat room temperature, and the mixture was stirred at room temperature for 18 hours
  2. extractionorganic matter was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a crude product
  8. customThis crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-ethyl acetate)

Sources & evidence

ORD record
ord-972624bfb14840b5ab66fc1b91bab6aa
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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