Hydrochloric Acid → 4-Cyano-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-6-carboxylic Acid

HRID 17610

Reaktionsgleichung

Reaktionsgleichung von HRID 17610
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:17]#[N:18])[C:10]([CH3:16])=[C:11]([CH:14]=[O:15])[C:12]=3[F:13])[N:8]=2)[CH2:3][CH2:2]1.O.O.P([O-])(O)(O)=[O:22].[Na+].CC(=CC)C.Cl([O-])=O.[Na+].Cl>C(O)(C)(C)C.O.O1CCCC1.C(OCC)(=O)C>[C:17]([C:9]1[C:7]2[N:8]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[O:5][C:6]=2[C:12]([F:13])=[C:11]([C:14]([OH:22])=[O:15])[C:10]=1[CH3:16])#[N:18]

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 860975112-Cyclopropyl-7-fluoro-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685873884-Cyano-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-6-carboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Cyclopropyl-7-fluoro-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile (I-182) (160 mg, 0.66 mmol) was dissolved in tert-butanol (4.5 ml)-water (3 ml)-tetrahydrofuran (3 ml), then at 0° C., sodium dihydrogenphosphate dihydrate (153 mg, 0.98 mmol), 2-methyl-2-butene (292 μl, 2.62 mmol), sodium chlorite (purity 80%, 222 mg, 1.97 mmol) were added. This was stirred for 15 hours with gradually warming up to room temperature. At 0° C., aqueous 1 N hydrochloric acid solution and ethyl acetate were added to the reaction liquid, followed by stirring at the same temperature for 10 minutes. The aqueous layer was separated, and extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away to obtain the entitled compound. This was used in the next reaction as such.

Aufarbeitung

  1. stirringby stirring at the same temperature for 10 minutes
  2. customThe aqueous layer was separated
  3. extractionextracted twice with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customto obtain the entitled compound
  9. customThis was used in the next reaction as such

Quellen und Nachweise

ORD-Eintrag
ord-a0ac29dabbb840a9bd73081a2eac2471
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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