Water → HCID 86606502, compound

HRID 229377Notes

Reaction equation

HRID 229377 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)(Cl)=O.[CH2:11]([CH:13]1[N:22]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([CH3:34])[CH:27]=2)(=[O:25])=[O:24])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:35])[CH:20]=2)[N:15]2[CH:36]=[CH:37][CH:38]=[C:14]12)[CH3:12].O>C(Cl)Cl>[CH2:11]([CH:13]1[N:22]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([CH3:34])[CH:27]=2)(=[O:25])=[O:24])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:35])[CH:20]=2)[N:15]2[C:36]([CH:4]=[O:5])=[CH:37][CH:38]=[C:14]12)[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 69064665HCID 69064665, compound

Product 1

HCID 86606502HCID 86606502, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 25 ml round bottom flask under nitrogen charged with 10 ml of methylene chloride was added 0.1 ml (1.25 mmol) of DMF and cooled to 0° C. Added 0.12 ml of phosphorous oxychloride and stirred for 15 minutes. 0.40 g (1 mmol) of the product from Example 18 was added and the mixture was stirred at room temperature for 16 hours. At the end of this time added 5 ml of water and stirred vigorously an additional 0.5 hr. The solution was diluted with methylene chloride and the layers separated. The aqueous phase was extracted with methylene chloride and combined with the previous layer. After drying (MgSO4) and concentrating the crude solid was subjected to column chromatography on silica gel, eluting with 30% ethyl acetate:hexane. The product was collected and briefly characterized, then used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. stirringstirred vigorously an additional 0.5 hr
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with methylene chloride
  5. dry with materialAfter drying (MgSO4)
  6. concentrationconcentrating the crude solid
  7. washeluting with 30% ethyl acetate
  8. customThe product was collected
  9. customused in the next step without further purification

Sources & evidence

ORD record
ord-2a24d72cf1694e6aababbb9b0374c8ce
Source dataset
uspto-grants-2009_07
Patent number
US07563793B2

Reaction notes

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