Triethylamine → phenyl 2-{4-[2-ethyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]phenyl}ethylcarbamate

HRID 967835

반응식

HRID 967835 반응식
[CH2:1]([C:3]1[N:4]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26](C)([CH3:28])[CH3:27])=[CH:17][CH:16]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:7]=1)[CH3:2].C(N(CC)CC)C.ClC(O[C:42]1[CH:47]=CC=C[CH:43]=1)=O>Cl.CO>[CH2:1]([C:3]1[N:4]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]3[CH:27]=[CH:47][CH:42]=[CH:43][CH:28]=3)=[CH:19][CH:20]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:7]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 22291428tert-butyl 2-{4-[2-ethyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]phenyl}ethylcarbamate

생성물 1

HCID 22291420phenyl 2-{4-[2-ethyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]phenyl}ethylcarbamate수율 85%

시약·촉매·용매 1

HCID 21893726Hydrochloride methanol용매

실험 절차

A solution of tert-butyl 2-{4-[2-ethyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]phenyl}ethylcarbamate (1.1 g, 2.6 mmol) in 10% HCl-MeOH (20 mL) was heated at 50° C. for 2 h. After cooling, the volatile components were removed by evaporation and the resulting amorphous was dried under reduced pressure. Then, the amorphous was suspended in dichloromethane at 0° C. To the cooled mixture was added triethylamine (1.4 mL, 10 mmol) and phenyl chloroformate (380 μL, 3.0 mmol). After 1 h, the reaction mixture was partitioned between ethyl acetate (30 mL) and water (10 mL). The aqueous phase was extracted with ethyl acetate (3×30 mL) and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 3:1 to 2:1) afforded 924 mg (85%) of the title compound as colorless amorphous. MS (ESI) m/z 430 [M+H]+.

후처리

  1. temperatureAfter cooling
  2. customthe volatile components were removed by evaporation
  3. customthe resulting amorphous was dried under reduced pressure
  4. customwas suspended in dichloromethane at 0° C
  5. customthe reaction mixture was partitioned between ethyl acetate (30 mL) and water (10 mL)
  6. extractionThe aqueous phase was extracted with ethyl acetate (3×30 mL)
  7. dry with materialthe combined organic phase was dried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 3:1 to 2:1)

출처 및 근거

ORD 기록
ord-239a9de491104a80ae7cd98ee83de147
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956050B2

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