2-Hydroxyimidazole → 1-[2-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-oxo-ethyl]-1,3-dihydro-imidazol-2-one

HRID 1604424노트

반응식

HRID 1604424 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].N1C=CNC1=[O:16].COC1C=C(CC[N:29]2[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=3)[C:30]2=[O:46])C=CC=1OC.[CH2:47]([C:51](C)=O)[CH:48](C)[CH3:49].O>CN(C=O)C>[CH:45]1([O:44][C:38]2[CH:37]=[C:36]([C:35](=[O:16])[CH2:34][N:31]3[CH:32]=[CH:33][NH:29][C:30]3=[O:46])[CH:41]=[CH:40][C:39]=2[O:42][CH3:43])[CH2:49][CH2:48][CH2:47][CH2:51]1

참가 물질

6

반응물 4

HCID 222082-HydroxyimidazoleHCID 2724254Sodium bis(trimethylsilyl)amideHCID 224568231,3-bis[2-(3,4-dimethoxyphenyl)ethyl]-1,3,4,5-tetrahydro-2H-imidazol-2-oneHCID 22737866Isobutyl methyl ketone water

생성물 1

HCID 99269351-[2-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-oxo-ethyl]-1,3-dihydro-imidazol-2-one수율 12.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium bis(trimethylsilyl)amide (5 ml) was added to a solution of 1,3-dihydro-2H-imidazol-2-one (0.84 g) in DMF (50 ml), stirred under a N2 flow and cooled in an ice-bath. The reaction mixture was stirred for 30 minutes. Intermediate 1 (2.69 g) was added portionwise and the resulting reaction mixture was stirred for 16 hours at RT, then for 2 hours at 50° C. The reaction mixture was stirred in methyl isobutyl ketone/water (200 ml/50 ml). The solvent was evaporated and methyl isobutyl ketone (100 ml) was added and azeotroped on the rotary evaporator. The mixture was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 97/3). The desired fractions were collected and the solvent was evaporated. The white solid was stirred in diisopropyl ether, filtered off, washed with DIPE and dried, yielding 0.4 g (12.6%) of 1-[2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-oxo-ethyl]-1,3-dihydro-2H-imidazol-2-one (interm. 2; mp. 201.1° C.).

후처리

  1. temperaturecooled in an ice-bath
  2. stirringThe reaction mixture was stirred for 30 minutes
  3. customthe resulting reaction mixture
  4. stirringwas stirred for 16 hours at RT
  5. customThe solvent was evaporated
  6. additionmethyl isobutyl ketone (100 ml) was added
  7. customazeotroped on the rotary evaporator
  8. customThe mixture was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 97/3)
  9. customThe desired fractions were collected
  10. customthe solvent was evaporated
  11. stirringThe white solid was stirred in diisopropyl ether
  12. filtrationfiltered off
  13. washwashed with DIPE
  14. customdried

출처 및 근거

ORD 기록
ord-99bcdae4a4e8401787bf7a9cfc7535b5
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05994376

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