Toluene → HCID 68884464, 화합물

HRID 1294332

반응식

HRID 1294332 반응식
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14]C1C=CC(CO)=CC=1.[O:23]=[C:24]1[C:29]([CH2:30][C:31]([O:33]C)=[O:32])=[CH:28][CH:27]=[CH:26][NH:25]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O:63][CH2:64][CH3:65])=O)=NC(OCC)=O.[C:66]1([CH3:72])[CH:71]=CC=[CH:68][CH:67]=1>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:63][C:64]1[CH:65]=[CH:71][C:66]([CH2:72][O:23][C:24]2[C:29]([CH2:30][C:31]([OH:33])=[O:32])=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:67][CH:68]=1

참가 물질

7

반응물 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 17861222HCID 17861222, 화합물HCID 545680024-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethyl]benzyl alcohol

생성물 1

HCID 68884464HCID 68884464, 화합물수율 14%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of [4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]methanol (0.87 g), methyl 2-(2-oxo-1,2-dihydro-3-pyridyl)acetate (0.36 g), triphenylphosphine (0.87 g) and tetrahydrofuran (50 mL) was dropwise added a solution (40%, 1.47 g) of diethyl azodicarboxylate in toluene at room temperature, and the mixture was stirred for 15 hrs. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography to give an oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v). To a mixture of the obtained oil, tetrahydrofuran (3 mL) and methanol, (3 mL) was added an 1N aqueous sodium hydroxide solution (3 mL) and the mixture was stirred at room temperature for 2 hrs. 1N Hydrochloric acid (3 mL) and water were added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give crystals (0.14 g, 14%) of 2-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyloxy]-3-pyridyl]acetic acid from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 134-135° C.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customto give an oil from a fraction
  3. washeluted with ethyl acetate-hexane (1:3
  4. additionTo a mixture of the obtained oil, tetrahydrofuran (3 mL) and methanol, (3 mL)
  5. additionwas added an 1N aqueous sodium hydroxide solution (3 mL)
  6. stirringthe mixture was stirred at room temperature for 2 hrs
  7. addition1N Hydrochloric acid (3 mL) and water were added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-aae04f1737cb4ecc803c8349e6cd9200
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238716B2

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