Water → HCID 24969673, compound

HRID 661447Notes

Reaction equation

HRID 661447 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[F:15][C:16]([F:32])([F:31])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C@H:24]([CH2:29][CH3:30])[CH2:25][C:26]([OH:28])=O)=[CH:19][CH:18]=1.O>CS(O)(=O)=O>[CH2:29]([C@@H:24]1[CH2:25][C:26](=[O:28])[C:19]2[C:20](=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:32])[F:31])[CH:18]=2)[NH:23]1)[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 14812Phosphorus oxide (P4O10)HCID 57972811HCID 57972811, compound

Product 1

HCID 24969673HCID 24969673, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Phosphorus pentoxide (13.1 kg) was dissolved in methanesulfonic acid (131 liter) warmed, the solution was added to the compound (26.27 kg) obtained in Example 2 (1) above and the mixture was stirred at 65-75° C. for about 3 hours. To the reaction mixture, was added water (342 liter) dropwise while keeping the temperature at 10-50° C., and then the solution was cooled at below 10° C. The precipitated crystalline was collected by filtration and washed with water (393 liter). When the pH of the washing was acidic, the precipitate was washed again. The wet crystalline was dissolved in ethyl acetate (26.3 liter) and n-heptane (105 liter) at 60-70° C., and n-heptane (158 liter) was further added at the same temperature. The solution was stirred at 45-50 for about 3 hours, cooled to below 10° C., and the precipitated crystalline was filtered and washed with ethyl acetate/n-heptane=1/10 (26.3 liter). The wet product was dried under reduced pressure at below 50° C. to give the titled compound (11.5 kg, yield 47%). MS (APCI) m/z: 244 [M+H]+.

Workup

  1. temperaturewarmed
  2. customat 10-50° C.
  3. temperaturethe solution was cooled at below 10° C
  4. filtrationThe precipitated crystalline was collected by filtration
  5. washwashed with water (393 liter)
  6. washthe precipitate was washed again
  7. dissolutionThe wet crystalline was dissolved in ethyl acetate (26.3 liter)
  8. additionn-heptane (105 liter) at 60-70° C., and n-heptane (158 liter) was further added at the same temperature
  9. stirringThe solution was stirred at 45-50 for about 3 hours
  10. temperaturecooled to below 10° C.
  11. filtrationthe precipitated crystalline was filtered
  12. washwashed with ethyl acetate/n-heptane=1/10 (26.3 liter)
  13. customThe wet product was dried under reduced pressure at below 50° C.

Sources & evidence

ORD record
ord-1a540b07ae9d439bbdd724abe63dad42
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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