Hydrochloric Acid → 3-(4-Fluorophenyl)-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid

HRID 1676355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676355
[Li+].[OH-].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH:14]3[C:12]([C:16]([O:18]C)=[O:17])([CH2:13]3)[C:11]2=[O:20])=[CH:6][CH:5]=1.Cl>C1COCC1.O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH:14]3[C:12]([C:16]([OH:18])=[O:17])([CH2:13]3)[C:11]2=[O:20])=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67348734HCID 67348734, Verbindung

Produkt 1

HCID 673496483-(4-Fluorophenyl)-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acidAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

LiOH (0.2 g, 8.4 mmol) was added into a suspension of methyl 3-(4-fluorophenyl)-2-oxo-3-aza-bicyclo[3.1.0]hexane-1-carboxylate (1.2 g, 4.8 mmol) in THF (20 mL) and water (1 mL). The reaction was allowed to stir for 1 hour. The reaction mixture was poured into water and neutralized with 1M HCl. The mixture was extracted with EtOAc, washed with brine, dried with Na2SO4, filtered and concentrated to afford the title compound (1 g, 79% yield) as a light brown solid. LRMS (APCI pos) m/e 235.9 (M+1). 1H NMR: (DMSO-d6, 400 MHz): δ 12.70 (br s, 1H), 7.57-7.62 (m, 2H), 7.17-7.23 (m, 2H), 4.06 (dd, 1H), 3.70 (dd, 1H), 2.50-2.56 (m, 1H), 1.76-1.81 (m, 1H), 1.29-1.33 (dd, 1H).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8b2ca2844edb4e8587b0ddcc0f114e25
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003662B2

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