Ammonium Chloride → HCID 131725943, compound

HRID 2214426Notes

Reaction equation

HRID 2214426 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C([O:14][P:15]([CH2:21][P:22]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH2:37])([O:24][CH2:25][CH3:26])=[O:23])(=[O:20])[O:16]C(C)C)(C)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:48])(=O)=O)=CC=1.[Cl-].[NH4+]>O1CCCC1.O>[F:48][O:14][P:15]([CH2:21][P:22]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH2:37])([O:24][CH2:25][CH3:26])=[O:23])(=[O:20])[OH:16]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 588007N-FluorobenzenesulfonimideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 21054116HCID 21054116, compound

Product 1

HCID 131725943HCID 131725943, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A 1 M solution of sodium bistrimethylsilylamide in tetrahydrofuran (30 mL, 30 mmol) was added dropwise with stirring to ((10-undecenyl)-ethoxyphosphinyl) methylphosphonic acid diisopropyl ester (11 g, 25.9 mmol) in anhydrous tetrahydrofuran (100 mL) at −78° C. under a nitrogen atmosphere. After the addition was complete (15 minutes) the solution was stirred for 45 minutes after which n-fluorobenzenesulfonimide (10 g, 31.7 mmol) in anhydrous tetrahydrofuran (30 mL) was added. The reaction was stirred for 3 hours at −78° C. The reaction was then warmed to −50° C., and excess base was neutralized by the addition of saturated ammonium chloride. The mixture was warmed to room temperature and the volatiles were removed by rotary evaporation to give a creamy solid. The solid was dissolved in water (300 mL) and then extracted three times with ethyl acetate (350 mL). The organic layers were combined and extracted with saturated sodium bicarbonate (250 mL). The ethyl acetate layer was dried over sodium sulfate and volatiles were removed by rotary evaporation to give a viscous liquid. The liquid was purified by flash chromatography (500 g silica, ethyl acetate/ethanol=9.5/0.5) to give the desired product (3.1 g, 27% yield).

Workup

  1. additionAfter the addition
  2. custom(15 minutes)
  3. additionwas added
  4. temperatureThe reaction was then warmed to −50° C.
  5. temperatureThe mixture was warmed to room temperature
  6. customthe volatiles were removed by rotary evaporation
  7. customto give a creamy solid
  8. extractionextracted three times with ethyl acetate (350 mL)
  9. extractionextracted with saturated sodium bicarbonate (250 mL)
  10. dry with materialThe ethyl acetate layer was dried over sodium sulfate and volatiles
  11. customwere removed by rotary evaporation
  12. customto give a viscous liquid
  13. customThe liquid was purified by flash chromatography (500 g silica, ethyl acetate/ethanol=9.5/0.5)

Sources & evidence

ORD record
ord-855977a28bd7467ab19328bf0223ed4d
Source dataset
uspto-grants-2006_09
Patent number
US07109184B2

Reaction notes

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