Sodium hydride → HCID 58645854, compound

HRID 1765322Notes

Reaction equation

HRID 1765322 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH2:14]([O:21][C:22]([NH:24][CH:25]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=O)[CH2:26]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>COCCOC.O>[CH2:14]([O:21][C:22]([NH:24][CH:25]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=[CH:3][C:1]#[N:2])[CH2:26]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 21107062HCID 21107062, compound

Product 1

HCID 58645854HCID 58645854, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of diethyl (cyanomethyl)phosphonate (0.189 mL) in 1,2-dimethoxyethane (1 mL) at room temperature under nitrogen was added 60% sodium hydride oil dispersion (46 mg). Upon completion of addition, the mixture was stirred for 1 h. After this time, a solution of 3-benzyloxycarbonylamino-1-oxo-1,2,3,4-tetrahydronaphthalene (69 mg) in 1,2-dimethoxyethane was added (1 mL). The reaction mixture was stirred at room temperature for 1 h, and then heated to reflux for 4 h. At the conclusion of this period, the reaction mixture was cooled to room temperature, diluted with water, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated under vacuum to yield a residue. The residue was purified by reverse phase preparative HPLC (trifluoroacetic acid containing solvents were used) to obtain the title compound (38 mg) as a mixture of olefin isomers.

Workup

  1. additionUpon completion of addition
  2. stirringThe reaction mixture was stirred at room temperature for 1 h
  3. temperatureheated
  4. temperatureto reflux for 4 h
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customevaporated under vacuum
  8. customto yield a residue
  9. customThe residue was purified by reverse phase preparative HPLC (trifluoroacetic acid containing solvents were used)

Sources & evidence

ORD record
ord-b29b6846f8e3493182b10ef9e500898b
Source dataset
uspto-grants-2007_06
Patent number
US07226942B2

Reaction notes

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