Phosphoric Acid → HCID 86740257, compound

HRID 1380578Notes

Reaction equation

HRID 1380578 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=O.P(=O)(O)(O)O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:28]([C:30]1[C:34]([C:35]2[NH:36][C:37]3[C:42]([CH:43]=2)=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:33]([CH3:44])[O:32][N:31]=1)[CH3:29]>C(#N)C.CCOCC.O>[CH2:28]([C:30]1[C:34]([C:35]2[NH:36][C:37]3[C:42]([C:43]=2[C:4](=[O:6])[CH2:3][CH2:2][C:1]([O:8][CH3:9])=[O:7])=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:33]([CH3:44])[O:32][N:31]=1)[CH3:29]

Participants

8

Reactant 4

HCID 1004Phosphoric AcidHCID 9845Trifluoroacetic anhydrideHCID 6930703Mono-Methyl SuccinateHCID 130386862-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indole

Product 1

HCID 86740257HCID 86740257, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of 59.4 grams (0.45 mole) of mono-methyl succinate in 300 ml acetonitrile is treated by dropwise addition with 5.5 grams of 85% phosphoric acid and then by dropwise addition with 63.5 ml (0.45 mole) of trifluoroacetic acid anhydride. The mixture is stirred 15 minutes at room temperature and then treated by dropwise addition with 33.9 grams (0.15 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-indole in 300 ml of acetonitrile. The mixture is stirred at room temperature overnight, after which 1.5 liters of water and 1 liter of ether are added. The two layers are separated, and the ether is washed with water and made basic by the addition of solid sodium carbonate and water. The mixture is stirred 1 hour at room temperature, following which the layers are separated. The ether layer is then washed with water, dried over MgSO4, filtered and evaporated to give the title compound.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. customThe two layers are separated
  3. washthe ether is washed with water
  4. additionmade basic by the addition of solid sodium carbonate and water
  5. stirringThe mixture is stirred 1 hour at room temperature
  6. customare separated
  7. washThe ether layer is then washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-058c93c29e0d4114b2dde6412f9c3cef
Source dataset
uspto-grants-1986_04
Patent number
US04582848

Reaction notes

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