Hydrochloric Acid → rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid

HRID 38775

Reaktionsgleichung

Reaktionsgleichung von HRID 38775
C12CC(CC1)CC2[O:8][C:9]([C:11]1[C:12]([C:25]([F:28])([F:27])[F:26])=[N:13][C:14]([O:17][C@@H:18]2[CH2:23][C@@H:22]3[CH2:24][C@H:19]2[CH2:20][CH2:21]3)=[N:15][CH:16]=1)=[O:10].C12CC(CC1)CC2OC(C1C(C(F)(F)F)=NC(O[C@H]2C[C@H]3C[C@@H]2CC3)=NC=1)=O.[OH-].[Na+].Cl>C(O)C>[C@H:19]12[CH2:24][C@H:22]([CH2:21][CH2:20]1)[CH2:23][C@H:18]2[O:17][C:14]1[N:13]=[C:12]([C:25]([F:26])([F:27])[F:28])[C:11]([C:9]([OH:10])=[O:8])=[CH:16][N:15]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66720285rac-(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylateHCID 66720386rac-(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl2-[(1S,2S,4R)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylate

Produkt 1

HCID 66720184rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylic acidAusbeute 130 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of a mixture (110 mg) of rac-(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylate and rac-(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl2-[(1S,2S,4R)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylate in ethanol (3 mL) was added a 1 M aqueous sodium hydroxide solution (1 mL) at room temperature, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added 1 M hydrochloric acid (1 mL), and then the solvent was evaporated under reduced pressure. To the residue was added water, followed by extraction with ethyl acetate. The extracted organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and then the obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol=98:2 to 90:10) to obtain rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid (109 mg) as a colorless solid.

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. additionTo the residue was added water
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extracted organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol=98:2 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-55da990513074a67b6c523f9d6cbb319
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524727B2

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