Dimethylformamide → HCID 178470653, compound

HRID 220163Notes

Reaction equation

HRID 220163 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-4598355ee02a4a0689f63b10a85e1693
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

Loading…