Sodium Hydroxide → 3-[4-(Trifluoromethoxy)phenyl]-2-{[4-(3,3,3-trifluoropropoxy)benzoyl]amino}propanoic acid

HRID 1799278

Reaktionsgleichung

Reaktionsgleichung von HRID 1799278
C(Cl)(=O)C(Cl)=O.[F:7][C:8]([F:22])([F:21])[CH2:9][CH2:10][O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1.[OH-].[Na+].Cl.[NH2:26][CH:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][CH:33]=1)[C:28]([OH:30])=[O:29]>CN(C=O)C.C1COCC1.O.C(Cl)Cl>[F:40][C:39]([F:41])([F:42])[O:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][CH:27]([NH:26][C:16](=[O:18])[C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][C:8]([F:7])([F:22])[F:21])=[CH:20][CH:19]=2)[C:28]([OH:30])=[O:29])=[CH:37][CH:36]=1

Komponenten

9

Edukt 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 226033402-Amino-3-[4-(trifluoromethoxy)phenyl]propanoic acid hydrochlorideHCID 581116554-(3,3,3-Trifluoropropoxy)benzoic acid

Produkt 1

HCID 780686233-[4-(Trifluoromethoxy)phenyl]-2-{[4-(3,3,3-trifluoropropoxy)benzoyl]amino}propanoic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

DMF (three drops) and oxalyl chloride (3.50 mL, 40.0 mmol) were added to a methylene chloride (35 mL) solution of 4-(3,3,3-trifluoropropoxy)benzoic acid (4.68 g, 20.0 mmol) obtained in preparation process of Example 33 (33a), under ice-cooling with stirring. The mixture was stirred at room temperature for 3.5 hours, and then the solvent was evaporated. The obtained residue was dissolved in THF (20 mL). This solution and a 1 M sodium hydroxide aqueous solution (20 mL) were added dropwise simultaneously under ice-cooling with stirring to a solution mixture of a 1 M sodium hydroxide aqueous solution (40 mL) of 2-amino-3-[4-(trifluoromethoxy)phenyl]propanoic acid hydrochloride (5.71 g, 20.0 mmol) prepared in Reference Example 2, water (20 mL), and THF (15 mL). The resulting mixture was stirred under ice-cooling for 70 minutes, and then the solvents (mainly THF) were evaporated. Water was added to the residue, and the resulting mixture was changed to acidic by adding 2 M hydrochloric acid thereto. The precipitated crystalline solid was collected by filtration, washed with water and n-hexane, and dried under reduced pressure to give 8.75 g of the title compound (white powder, yield: 94%).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 3.5 hours
  3. customthe solvent was evaporated
  4. dissolutionThe obtained residue was dissolved in THF (20 mL)
  5. additionThis solution and a 1 M sodium hydroxide aqueous solution (20 mL) were added dropwise simultaneously under ice-
  6. temperaturecooling
  7. stirringThe resulting mixture was stirred under ice-
  8. temperaturecooling for 70 minutes
  9. customthe solvents (mainly THF) were evaporated
  10. additionWater was added to the residue
  11. additionby adding 2 M hydrochloric acid
  12. filtrationThe precipitated crystalline solid was collected by filtration
  13. washwashed with water and n-hexane
  14. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-71d7b0d792ed4baea40d3be601e63468
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344029B2

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