Water → HCID 67361561, compound

HRID 404399Notes

Reaction equation

HRID 404399 reaction equation
[CH3:1][C:2]([CH3:29])([CH3:28])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[F:21])=[C:9]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=O)[CH:8]=1)=[O:4].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)S2)=CC=1.O.[CH:53]([NH:55][NH2:56])=O>C1(C)C=CC=CC=1>[CH3:29][C:2]([CH3:1])([CH3:28])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[F:21])=[C:9]([C:22]2[N:24]([CH:25]([CH3:26])[CH3:27])[CH:53]=[N:55][N:56]=2)[CH:8]=1)=[O:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 12229HydrazinecarboxaldehydeHCID 87949Lawesson's reagentHCID 67359702HCID 67359702, compound

Product 1

HCID 67361561HCID 67361561, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a room temperature solution of 29.3 (244 mg, 608 μmol) in toluene was added 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (369 mg, 912 μmol, Acros Organics). The mixture was heated at 120° C. for 1.0 hour, cooled to room temperature, treated with water, and then extracted with EtOAc. After removal of organic solvent under reduced pressure, the residue was dissolved in dioxane (4 mL). To the solution was added formohydrazide (208 mg, 3461 μmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) and mercuric acetate (202 μL, 2076 μmol, Acros Organics). The resulting mixture was heated at 130° C. for 1.5 hours, cooled to room temperature, treated with water, and extracted with 30% IPA. After removal of organic solvents under reduced pressure, purification of the residue by flash chromatography on silica gel with 0-60% EtOAc/hexanes for elution gave 29.4 as a colorless oil (135 mg, 52%).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. customAfter removal of organic solvent under reduced pressure
  4. dissolutionthe residue was dissolved in dioxane (4 mL)
  5. temperatureThe resulting mixture was heated at 130° C. for 1.5 hours
  6. temperaturecooled to room temperature
  7. extractionextracted with 30% IPA
  8. customAfter removal of organic solvents
  9. customunder reduced pressure, purification of the residue by flash chromatography on silica gel with 0-60% EtOAc/hexanes
  10. washfor elution

Sources & evidence

ORD record
ord-a73a629dcb55474fba46e4e708336a94
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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