Benzoic Acid → [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoate

HRID 1491702노트

반응식

HRID 1491702 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@H:12]([OH:14])[CH3:13])[CH2:11][O:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34](O)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O.C(OCC)(=O)C>[C:34]([O:14][C@H:12]([C@@:9]1([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH2:11][O:10]1)[CH3:13])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

참가 물질

8

반응물 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10536015(1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol

생성물 1

HCID 10709605[(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoate수율 78.5%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (16.1 g) in tetrahydrofuran (320 ml) were added triphenylphosphine (63.3 g), benzoic acid (29.5 g) and diethyl azodicarboxylate (42.0 g) under ice-cooling. The mixture was stirred for 6 hours at room temperature under argon atmosphere. To the reaction mixture were added ethyl acetate (800 ml) and water (500 ml). The separated aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layers were washed with water and a saturated saline, dried over magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=15:1→7:1) for purification to give [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] benzoate (19.2 g) as a colorless oily substance.

후처리

  1. temperaturecooling
  2. extractionThe separated aqueous layer was extracted with ethyl acetate (200 ml)
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated saline, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=15:1→7:1) for purification

출처 및 근거

ORD 기록
ord-ae44b8129ab74158b5526bb2a15a10e1
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05371100

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