tert-Butyl (2E)-but-2-enoylcarbamate → 1,1-dimethylethyl (3-{[4-(4-methyl-1H-imidazol-1-yl)phenyl]amino}butanoyl)carbamate

HRID 2041705

반응식

HRID 2041705 반응식
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH:6]=1.[C:14]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:18])/[CH:15]=[CH:16]/[CH3:17]>C(#N)C.O.O.O.O.O.O.[N+]([O-])([O-])=O.[Y+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][CH:16]([CH3:17])[CH2:15][C:14]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])=[CH:9][CH:8]=2)[CH:6]=1

참가 물질

5

반응물 2

HCID 11298363tert-Butyl (2E)-but-2-enoylcarbamateHCID 160051704-(4-Methyl-1h-imidazol-1-yl)benzenamine

생성물 1

HCID 681848641,1-dimethylethyl (3-{[4-(4-methyl-1H-imidazol-1-yl)phenyl]amino}butanoyl)carbamate수율 33%

시약·촉매·용매 2

HCID 166833Yttrium (III) nitrate hexahydrate (1:3:6)촉매2회HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

A mixture of 4-(4-methyl-1H-imidazol-1-yl)aniline (for a preparation see intermediate 64) (500 mg, 2.89 mmol), 1,1-dimethylethyl (2E)-2-butenoylcarbamate (for a preparation see intermediate 65) (615 mg, 3.32 mmol) and Yttrium(III) Nitrate hexahydrate (111 mg, 0.289 mmol) in acetonitrile (2 mL) was heated at 50° C. for 15 h. An extra portion of Yttrium(III) Nitrate hexahydrate (111 mg, 0.289 mmol) was added to the mixture which was stirred for 7 more hours before being cooled to room temperature. Half of the solvent was removed in vacuo and the residue was partitioned between AcOEt (40 mL) and a saturated NaHCO3 aqueous solution (20 mL). The layers were separated and the organic phase was washed with brine (15 mL). The combined aqueous phases were extracted with AcOEt (35 mL) and the combined organic were dried over MgSO4 and concentrated in vacuovacuo. Purification of the residue by flash chromatography on silica gel (gradient:4 to 8% MeOH in DCM) gave a residue which was further purified by flash chromatography on silica gel (gradient:60-95% AcOEt in Hexanes) to give 1,1-dimethylethyl (3-{[4-(4-methyl-1H-imidazol-1-yl)phenyl]amino}butanoyl)carbamate (343 mg, 0.956 mmol, 33%) as a colourless sticky solid.

후처리

  1. temperaturebefore being cooled to room temperature
  2. customHalf of the solvent was removed in vacuo
  3. customthe residue was partitioned between AcOEt (40 mL)
  4. customThe layers were separated
  5. washthe organic phase was washed with brine (15 mL)
  6. extractionThe combined aqueous phases were extracted with AcOEt (35 mL)
  7. dry with materialthe combined organic were dried over MgSO4
  8. concentrationconcentrated in vacuovacuo
  9. customPurification of the residue by flash chromatography on silica gel (gradient:4 to 8% MeOH in DCM)
  10. customgave a residue which
  11. customwas further purified by flash chromatography on silica gel (gradient:60-95% AcOEt in Hexanes)

출처 및 근거

ORD 기록
ord-6c40932fe2ab439ba5a2adc367d1e5a2
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580957B2

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