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

HRID 482057노트

반응식

HRID 482057 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

In the same manner as in Reference Example 1, starting from 2-(2-fluorophenyl)-2-[(1R)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxyethyl]oxirane (synthesized by the method described in EP 0548553A), (1R)-1-[2-(2-fluorophenyl)-2-oxiranyl] ethanol was obtained. To a solution of this product (34.77 g) in tetrahydrofuran (600 ml) were added, with ice cooling, 127.21 g of triphenyl phosphine, 102.88 g of 3,5-dinitrobenzoic acid and 84.47g of diethyl azodicarboxylate, and the resulting mixture was stirred at room temperature for 7 hours under an atmosphere of argon. To the reaction solution were added 600 ml of ethyl acetate, 100 ml of diisopropyl ether and 800 ml of water to fractionate and the 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, then dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1) to give 23.15 g of [(1S)-1-[(2R)-2-(2-fluorophenyl)-2-oxiranyl)ethyl] 3,5-dinitrobenzoate as colorless needles.

후처리

  1. customsynthesized by the method
  2. customwas obtained
  3. extractionthe aqueous layer was extracted with ethyl acetate (600 ml, 400 ml)
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium chloride successively, then dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-d5f90598d1b243b4a89eff3ec918f657
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792780

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