Methyl morpholine oxide → 3,5-dichloro-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methylbenzamide

HRID 749455노트

반응식

HRID 749455 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[C:5]([N:7]([CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:11][CH:12]=C)[CH3:8])=[O:6].C[N+]1([O-])CC[O:29]CC1.OS([O-])=O.[Na+].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.C(O)(C)(C)C.O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[C:5]([N:7]([CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:11][CH:12]=[O:29])[CH3:8])=[O:6]

참가 물질

9

반응물 4

HCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 23667635Sodium periodateHCID 689786383,5-Dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide

생성물 1

HCID 112455783,5-dichloro-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methylbenzamide수율 69.6%

시약·촉매·용매 4

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 962Water용매3회HCID 6386tert-Butanol용매

실험 절차

3,5-Dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide (210 mg, 0.57 mmol) was dissolved in a mixture of acetone (4 mL), t-butyl alcohol (2 mL) and water (1 mL). OsO4 (2.5% in t-butyl alcohol, 0.080 mL, 0.006 mmol) was added together with 4-methylmorpholine-4-oxide (296 mg, 2.52 mmol). The solution was stirred under nitrogen at room temperature overnight and then an aqueous solution of NaHSO3 (39%, 6 mL) was added. The mixture was stirred for 30 min, diluted with water (25 mL) and then extracted twice with CH2Cl2. The organic solution was dried over Na2SO4 and then the solvent was evaporated. The residue (256 mg) was dissolved in a mixture of THF (3 mL) and water (1 mL) and to the resultant solution was added sodium periodate (135 mg, 0.63 mmol). The mixture was stirred at room temperature overnight, diluted with water (25 mL) and then extracted twice CH2Cl2. The combined organic solutions were dried over Na2SO4 and then the solvent was evaporated. There was obtained 146 mg (69%) of 3,5-dichloro-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methylbenzamide as an oil. 1H NMR (400 MHz, CDCl3): 2.6-3.9 (cm, 8H), 6.4-7.4 (cm, 7H), 9.8 (s, 1H); LCMS: m/z 369 (M+1)+.

후처리

  1. stirringThe mixture was stirred for 30 min
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe organic solution was dried over Na2SO4
  4. customthe solvent was evaporated
  5. dissolutionThe residue (256 mg) was dissolved in a mixture of THF (3 mL) and water (1 mL) and to the resultant solution
  6. stirringThe mixture was stirred at room temperature overnight
  7. extractionextracted twice CH2Cl2
  8. dry with materialThe combined organic solutions were dried over Na2SO4
  9. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-8298b7231c6040b092bbc1cae4078ed4
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402581B2

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