4-Fluorobenzylamine → tert-butyl (4S,5R)-2-[(4-fluorophenyl)methylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

HRID 18733

반응식

HRID 18733 반응식
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9](SC)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1>CO>[C:21]([O:20][C:18]([N:10]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:9]1[NH:33][CH2:32][C:31]1[CH:34]=[CH:35][C:28]([F:27])=[CH:29][CH:30]=1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

참가 물질

4

반응물 2

HCID 673264-FluorobenzylamineHCID 86596320cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester

생성물 1

HCID 68568680tert-butyl (4S,5R)-2-[(4-fluorophenyl)methylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate수율 41.6%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
100 °C

실험 절차

A mixture of intermediate 59 (1.0 g, 0.0027 mol), 4-fluorobenzylamine (0.372 mL, 0.00321 mol) and MeOH (0.4 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and partitioned between dichloromethane and water. The organic solution is separated, dried (MgSO4), and concentrated in vacuo. The residue is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (80:20-40:60) gives 0.50 g of the product 85. 1H NMR (CDCl3) δ 7.60-7.35 (m, 3 H), 7.15-6.90 (m, 10 H), 6.85-6.70 (m, 2 H), 5.50-5.30 (m, 2 H), 5.75-5.55 (m, 2 H), 1.12 (s, 9 H); MS: m/z 446 (M++1).

후처리

  1. temperatureThe reaction mixture is cooled to RT
  2. custompartitioned between dichloromethane and water
  3. customThe organic solution is separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography on silica gel
  7. washgradient elution with heptane:EtOAc (80:20-40:60)

출처 및 근거

ORD 기록
ord-90f66e9dad814cf0bfd4b08022c1fd35
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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