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Acetonitrile → 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester

HRID 457388
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HRID 457388 반응식
[CH2:1]([N:5]1[C:9]([CH2:10][NH:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:8]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:7]=[C:6]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:2][CH2:3][CH3:4].[C:33]([O:37][C:38]([C:40]1[CH:47]=[CH:46][C:43]([CH2:44]Br)=[CH:42][CH:41]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34].[C:48](=[O:51])([O-])[O-:49].[K+].[K+].[C:54](#N)C>>[C:33]([O:37][C:38](=[O:39])[C:40]1[CH:47]=[CH:46][C:43]([CH2:44][N:11]([CH2:10][C:9]2[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:7][C:8]=2[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:42][C:41]=1[O:49][C:48](=[O:51])[CH3:54])([CH3:36])([CH3:35])[CH3:34]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 11414578Tert-butyl 4-(bromomethyl)benzoateHCID 58818024[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine

생성물 1

HCID 588179794-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester

실험 절차

To a solution of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine (4.0 g, 9.31 mmol) and 3-acetoxy]-4-tert-butoxycarbonyl-benzyl bromide (3.37 g, 10.24 mmol, 1.1 eq.) in 50 ml anhydrous acetonitrile is added anhydrous potassium carbonate (2.82 g, 20.5 mmol, 2.2 eq.), the resulting mixture is stirred at room temperature for 1 h, then raised to 50° C., stirred overnight. The solid precipitate is filtered off, washed with ethyl acetate, the combined organics is concentrated to dryness, purified through silica gel flash chromatography to give 3.99 g of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester MS (+VE) m/z 680 (M+1).

후처리

  1. temperatureraised to 50° C.
  2. stirringstirred overnight
  3. filtrationThe solid precipitate is filtered off
  4. washwashed with ethyl acetate
  5. concentrationthe combined organics is concentrated to dryness
  6. custompurified through silica gel flash chromatography

출처 및 근거

ORD 기록
ord-52c69b805f1242aea9464bb49dcf943e
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07186734B2

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