Sodium hydride → HCID 11685456, compound

HRID 1359948Notes

Reaction equation

HRID 1359948 reaction equation
[C:1]12[C:9](=[O:10])[C:8](=[O:11])[C:7]=1[NH:6][CH2:5][CH2:4][CH2:3][NH:2]2.[H-].[Na+].[CH:14]([P:16]([O:30][C:31]1[CH:32]=[C:33]([CH:39]=[CH:40][CH:41]=1)[C:34]([O:36][CH2:37][CH3:38])=[O:35])([O:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:17])=[CH2:15]>CN(C)C=O>[O:11]=[C:8]1[C:9](=[O:10])[C:1]2[N:2]([CH2:15][CH2:14][P:16]([O:30][C:31]3[CH:32]=[C:33]([CH:39]=[CH:40][CH:41]=3)[C:34]([O:36][CH2:37][CH3:38])=[O:35])([O:18][C:19]3[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=3)[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:17])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2826611HCID 2826611, compoundHCID 86233935HCID 86233935, compound

Product 1

HCID 11685456HCID 11685456, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 2.6-diaza-bicyclo[5.2.0]non-1(7)-ene-8,9-dione (2) (4 mmol, 608 mg) in N,N-dimethylformamide (60 mL) was treated under dry nitrogen and under stirring with 60% sodium hydride in oil (4.1 mmol, 164 mg). After 30 minutes at ambient temperature the yellow reaction mixture was cooled to 0° C. and a solution of diethyl 3,3′-[(vinylphosphoryl)bis(oxy)]dibenzoate (3) (4 mmol, 1.618 g) in N,N-dimethylformamide (30 mL) was added at once under vigorous stirring. The reaction mixture was then stirred at ambient temperature overnight, concentrated in vacuo and the residue partitioned between 5% aqueous ammonium chloride solution and ethyl acetate (2×60 mL). The organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness. The residue (>1.5 g) was flash chromatographed on silica gel (60 g). Elution with 2% methanol in chloroform afforded 600 mg (27%) of the desired title compound as a white powder; mp 116-7° C. MS (ES+): m/e 557.2 [M+H]+.

Workup

  1. additionwas treated under dry nitrogen
  2. concentrationconcentrated in vacuo
  3. customthe residue partitioned between 5% aqueous ammonium chloride solution and ethyl acetate (2×60 mL)
  4. washThe organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customchromatographed on silica gel (60 g)
  9. washElution with 2% methanol in chloroform

Sources & evidence

ORD record
ord-f4ff62e636f846fa89a20d0515c7123c
Source dataset
uspto-grants-2011_02
Patent number
US07879826B2

Reaction notes

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