3,5-Dinitrobenzoic acid → [(1S)-1-[(2R)-2-(2-fluorophenyl)-2-oxiranyl)ethyl] 3,5-dinitrobenzoate

HRID 1636679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1636679
FC1C=CC=CC=1C1([C@H](OC2CCCCO2)C)CO1.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1([C@H:30]([OH:32])[CH3:31])[CH2:29][O:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:52]([C:55]1[CH:56]=[C:57]([CH:61]=[C:62]([N+:64]([O-:66])=[O:65])[CH:63]=1)[C:58](O)=[O:59])([O-:54])=[O:53].N(C(OCC)=O)=NC(OCC)=O.C(OC(C)C)(C)C>O1CCCC1.O.C(OCC)(=O)C>[N+:52]([C:55]1[CH:56]=[C:57]([CH:61]=[C:62]([N+:64]([O-:66])=[O:65])[CH:63]=1)[C:58]([O:32][C@H:30]([C@@:27]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[F:20])[CH2:29][O:28]1)[CH3:31])=[O:59])([O-:54])=[O:53]

Komponenten

10

Edukt 6

HCID 74333,5-Dinitrobenzoic acidHCID 7914Diisopropyl EtherHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 538608792-(2-fluorophenyl)-2-[(1R)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxyethyl]oxiraneHCID 86749723(1R)-1-[2-(2-fluorophenyl)-2-oxiranyl]ethanol

Produkt 1

HCID 86749722[(1S)-1-[(2R)-2-(2-fluorophenyl)-2-oxiranyl)ethyl] 3,5-dinitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(2-Fluorophenyl)-2-[(1R)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxyethyl]oxirane (synthesized by the method described in EP0548553A) was converted into (1R)-1-[2-(2-fluorophenyl)-2-oxiranyl]ethanol by the method described in Reference Example 1. To an ice-cooled solution of this compound (34.77 g) in tetrahydrofuran (600 ml) were added triphenylphosphine (127.21 g), 3,5-dinitrobenzoic acid (102.88 g) and diethyl azodicarboxylate (84.47 g). The mixture was stirred at room temperature for 7 hours under an argon atmosphere, and then ethyl acetate (600 ml), diisopropyl ether (100 ml) and water (800 ml) were added. The separated aqueous layer was extracted with ethyl acetate (600 ml, 400 ml). The organic layers were combined, washed with water and a saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=5/1) and recrystallized from ethyl acetate to give [(1S)-1-[(2R)-2-(2-fluorophenyl)-2-oxiranyl]ethyl] 3,5-dinitrobenzoate (23.15 g) as colorless needles.

Aufarbeitung

  1. extractionThe separated aqueous layer was extracted with ethyl acetate (600 ml, 400 ml)
  2. washwashed with water
  3. dry with materiala saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=5/1)
  6. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1ea5eeff174844d28d0bb82641d552d4
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06034248

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