Dimethylformamide → HCID 178470653, compound

HRID 2042747Notes

Reaction equation

HRID 2042747 reaction equation
COP([CH2:7][C:8]([O:10][CH3:11])=[O:9])(OC)=O.[H-].[Na+].[F:14][C:15]([F:44])([F:43])[O:16][C:17]1[CH:42]=[CH:41][CH:40]=[CH:39][C:18]=1[CH2:19][O:20][C:21]1[NH:25][N:24]=[C:23]([C:26]2[CH:27]=[CH:28][C:29]([CH:32]3[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]3)=[N:30][CH:31]=2)[CH:22]=1.[CH3:45]N(C)C=O>>[F:14][C:15]([F:44])([F:43])[O:16][C:17]1[CH:42]=[CH:41][CH:40]=[CH:39][C:18]=1[CH2:19][O:20][C:21]1[NH:25][N:24]=[C:23]([C:26]2[CH:27]=[CH:28][C:29]([CH:32]3[CH2:37][CH2:36][C:35](=[CH:7][C:8]([O:10][CH2:11][CH3:45])=[O:9])[CH2:34][CH2:33]3)=[N:30][CH:31]=2)[CH:22]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 178515844HCID 178515844, compound

Product 1

HCID 178470653HCID 178470653, compound

Procedure

Methyl 2-(dimethoxyphosphoryl)acetate (0.76 ml, 3.77 mmol) was added dropwise to a stirred and cooled (0° C.) suspension of sodium hydride (0.15 g, 3.76 mmol) in dry N,N-dimethylformamide (10 mL). After 30 minutes of stirring at room temperature, a N,N-dimethylformamide solution of Example 93F (0.748 g, 1.71 mmol) was added to 0° C. After the addition, the solution was allowed to warm to room temperature and stir overnight. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic phases were washed with brine, dried (magnesium sulfate), filtered, and concentrated. The residue was purified by silica gel chromatography using 0 to 80% ethyl acetate, in hexanes to provide the title compound as a white solid.

Workup

  1. temperaturecooled
  2. stirringAfter 30 minutes of stirring at room temperature
  3. additionAfter the addition
  4. stirringstir overnight
  5. customThe reaction was quenched with saturated ammonium chloride solution
  6. extractionextracted with ethyl acetate
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5875aaa754a44d73ae06e5e5b9e4c65c
Source dataset
uspto-grants-2013_11
Patent number
US08586594B2

Reaction notes

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