Magnesium Chloride → Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate

HRID 17584

반응식

HRID 17584 반응식
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([CH:15](C(OC)=O)[C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:4]=1[CH3:30])#[N:2].[Cl-].[Mg+2].[Cl-]>CS(C)=O.O>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:4]=1[CH3:30])#[N:2]

참가 물질

5

반응물 2

HCID 5360315Magnesium ChlorideHCID 86630880Dimethyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)malonate

생성물 1

HCID 86630881Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate수율 90%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

Dimethyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)malonate (I-294) (2.887 g, 7.11 mmol) was dissolved in dimethyl sulfoxide (50 ml) and water (5 ml), then at room temperature, magnesium chloride (2.03 g, 21.34 mmol) was added. The solution was stirred at 90° C. for 23 hours, then cooled to room temperature. The solvent was evaporated away under reduced pressure, the residue was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=3:1, v/v) to obtain the entitled compound (2.216 g, 90%) as a pale yellow solid.

후처리

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated away under reduced pressure
  3. customThe aqueous layer was separated
  4. extractionextracted twice with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe insoluble matter was separated by filtration
  8. customthe solvent was evaporated away
  9. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

출처 및 근거

ORD 기록
ord-b74b11804c1f4443a72cecc559d303fe
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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