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Hydrochloric Acid → 7-(5-aminomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162903
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1162903
[N:1]([CH2:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:31])([F:30])[F:29])[NH:17][C:18]3=[O:21])=[CH:13][CH:12]=2)[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.Cl>O1CCCC1>[NH2:1][CH2:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:29])([F:31])[F:30])[NH:17][C:18]3=[O:21])=[CH:13][CH:12]=2)[CH2:6]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 118541917-(5-azidomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Produkt 1

HCID 118541927-(5-aminomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

The 7-(5-azidomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (50.0 mg, 0.116 mmol) obtained in Example 1-30 was dissolved in tetrahydrofuran (387 μl). Thereafter, triphenylphosphine (33.6 mg, 0.128 mmol) and water (20.9 μl) were added to the obtained solution, and the obtained mixture was then stirred at 40° C. for 14 hours. Thereafter, 1 N hydrochloric acid (0.5 ml) was added to the reaction solution, followed by washing with ethyl acetate. A 1 N sodium hydroxide aqueous solution (1.0 ml) was added to the residual water layer, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The obtained residue was purified by column chromatography using Bond Elut (registered trademark) NH2 (Varian; 1g), so as to obtain 7-(5-aminomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (45.8 mg; yield: 98%) in the form of a colorless foaming substance.

Aufarbeitung

  1. washby washing with ethyl acetate
  2. additionA 1 N sodium hydroxide aqueous solution (1.0 ml) was added to the residual water layer
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with a saturated saline solution
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe obtained residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2f49e85d4f5d483796b1b5dc23eca415
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07820693B2

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