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

HRID 1636679노트

반응식

HRID 1636679 반응식
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]

참가 물질

10

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1ea5eeff174844d28d0bb82641d552d4
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06034248

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