Toluene → HCID 68884464、化合物

HRID 1294332

反応式

HRID 1294332 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 68884464HCID 68884464、化合物収率 14%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aae04f1737cb4ecc803c8349e6cd9200
出典データセット
uspto-grants-2007_07
特許番号
US07238716B2

関連ノート

読み込み中…