Acetic Acid → HCID 21467012, compound

HRID 1939138Notes

Reaction equation

HRID 1939138 reaction equation
[NH2:1][C:2]1[C:3]([F:24])=[CH:4][C:5]([Cl:23])=[C:6]([NH:8][CH:9]([CH3:22])[C:10]([O:12][CH:13]2[CH:17]([O:18][C:19](=[O:21])[CH3:20])[CH2:16][O:15][CH2:14]2)=[O:11])[CH:7]=1.[C:25]1(=O)[O:30][C:28](=[O:29])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.C(O)(=O)C>O>[Cl:23][C:5]1[CH:4]=[C:3]([F:24])[C:2]([N:1]2[C:28](=[O:29])[C:27]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]3[C:25]2=[O:30])=[CH:7][C:6]=1[NH:8][CH:9]([CH3:22])[C:10]([O:12][CH:13]1[CH:17]([O:18][C:19](=[O:21])[CH3:20])[CH2:16][O:15][CH2:14]1)=[O:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6811Phthalic AnhydrideHCID 21467017HCID 21467017, compound

Product 1

HCID 21467012HCID 21467012, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.62 g of 4-acetoxytetrahydrofuran-3-yl 2-[(5-amino-2-chloro-4-fluorophenyl)amino]propionate, 0.80 g of phthalic anhydride, and 10 ml of acetic acid was heated under reflux for 3 hours while stirring. Water was added to the reaction mixture, and the semi-solid formed was collected by filtration, dissolved in ethyl acetate, washed successively with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane=2:3) to give 1.98 g of the title compound (Table 1, Compound No. 32).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customthe semi-solid formed
  4. filtrationwas collected by filtration
  5. dissolutiondissolved in ethyl acetate
  6. washwashed successively with a saturated aqueous solution of sodium hydrogencarbonate
  7. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate-hexane=2:3)

Sources & evidence

ORD record
ord-6b5681823a1d486ab6cb813094190c7f
Source dataset
uspto-grants-1997_12
Patent number
US05696056

Reaction notes

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