tert-Butanol → HCID 21062601、化合物

HRID 1243218ノート

反応式

HRID 1243218 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:5](C(O)=O)=[CH:4][C:3]=1[O:11][CH3:12].C([N:15]([CH2:18]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[C:37]([OH:41])([CH3:40])([CH3:39])[CH3:38]>C1(C)C=CC=CC=1>[C:37]([O:41][C:18]([NH:15][C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([O:11][CH3:12])[CH:4]=1)=[O:27])([CH3:40])([CH3:39])[CH3:38]

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 5984364-Fluoro-3-methoxybenzoic acid

生成物 1

HCID 21062601HCID 21062601、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

4-Fluoro-3-methoxybenzoic acid (1.00 g, 5.87 mmol) (from Example 34b supra) was dissolved in toluene (30 mL). Triethylamine (3.2 mL, 23.48 mmol) (Fisher), diphenyl phosphoryl azide (2.5 mL, 11.74 mmol) (Aldrich) and tert-butanol (6 mL) (Fisher) were successively added at room temperature. The reaction mixture was heated at reflux for 2 hours, then quenched at room temperature with 1 N aqueous hydrochloric acid (20 mL). The mixture was extracted with ethyl acetate and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, then dried over anhydrous sodium sulfate and filtered. Concentration under reduced pressure gave a yellow oil that was purified by flash chromatography (20% ethyl acetate in hexanes) to give (tert-butoxy)-N-(4-fluoro-3-methoxyphenyl)carboxamide as a white solid. (Yield 0.98 g, 70%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. customquenched at room temperature with 1 N aqueous hydrochloric acid (20 mL)
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe layers were separated
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationConcentration under reduced pressure
  10. customgave a yellow oil that
  11. customwas purified by flash chromatography (20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-8dc86a75603b494eb321b56cedea6abb
出典データセット
uspto-grants-2006_10
特許番号
US07115740B2

反応ノート

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