3,5-Dinitrobenzoic acid → HCID 86749722、化合物

HRID 279161

反応式

HRID 279161 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C@H:11]([OH:13])[CH3:12])[CH2:10][O:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:33]([C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([N+:45]([O-:47])=[O:46])[CH:44]=1)[C:39](O)=[O:40])([O-:35])=[O:34].N(C(OCC)=O)=NC(OCC)=O.C(OC(C)C)(C)C>O1CCCC1.O.C(OCC)(=O)C>[N+:33]([C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([N+:45]([O-:47])=[O:46])[CH:44]=1)[C:39]([O:13][C@H:11]([C@@:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:10][O:9]1)[CH3:12])=[O:40])([O-:35])=[O:34]

参加物

9

反応物 5

HCID 74333,5-Dinitrobenzoic acidHCID 7914Diisopropyl EtherHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86749723HCID 86749723、化合物

生成物 1

HCID 86749722HCID 86749722、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-(2-Fluorophenyl)-2-[(l1R)-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.

後処理

  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

出典と根拠

ORDレコード
ord-04f57a965b214a38bbfbe8ba3893900b
出典データセット
uspto-grants-2002_03
特許番号
US06362206B1

関連ノート

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