Sodium Chloride → HCID 57868856, compound

HRID 1692905Notes

Reaction equation

HRID 1692905 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][C:15]1([S:18]([N:21]2[CH2:24][C:23](=O)[CH2:22]2)(=[O:20])=[O:19])[CH2:17][CH2:16]1.[Na+].[Cl-]>O1CCCC1.O>[CH3:14][C:15]1([S:18]([N:21]2[CH2:24][C:23](=[CH:5][C:3]#[N:4])[CH2:22]2)(=[O:19])=[O:20])[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 57868868HCID 57868868, compound

Product 1

HCID 57868856HCID 57868856, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of sodium hydride (60% dispersion in mineral oil, 17 mg, 0.42 mmol) in tetrahydrofuran (2 mL) at 0° C. was added diethyl cyanomethylphosphonate (70 μL, 0.43 mmol) dropwise. The mixture was then allowed to reach room temperature and stir for a further 45 minutes. A solution of 1-[(1-methylcyclopropyl)sulfonyl]azetidin-3-one (prepared in Step 5) in tetrahydrofuran (1.0 mL) was added and the mixture was allowed to stir at ambient temperature for 16 hours. Into the reaction was added water and solid NaCl, and the product was extracted with three portions of ethyl acetate. The combined extracts were dried over sodium sulfate, decanted and concentrated to afford product (71 mg, 100%), used without further purification in Step 7.

Workup

  1. customto reach room temperature
  2. stirringto stir at ambient temperature for 16 hours
  3. extractionthe product was extracted with three portions of ethyl acetate
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe3dca36f6b64ac3b200519bdda591d2
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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