Cyclohexanemethylamine → tert-butyl (4S,5R)-2-(cyclohexylmethylamino)-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

HRID 18727

反応式

HRID 18727 の反応式
[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.[CH:27]1([CH2:33][NH2:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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:34][CH2:33][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

参加物

4

反応物 2

HCID 76688CyclohexanemethylamineHCID 86596320cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester

生成物 1

HCID 68567695tert-butyl (4S,5R)-2-(cyclohexylmethylamino)-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate収率 39%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of intermediate 59 (0.5 g, 1.36 mmol), cyclohexanemethylamine (0.53 mL, 6.1 mmol) and MeOH (0.11 mL) is heated at 100° C. for 48 h. The reaction mixture is cooled to RT and purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-50:50) gives 0.23 g of the product 79. 1H NMR (CDCl3) δ 7.80-7.35 (m, 2 H), 7.18 9s, 1 H), 7.10-6.90 (m, 6 H), 6.90-6.70 (m, 2 H), 5.45-5.30 (m, 2 H), 3.45-3.15 (m, 2 H), 2.00-1.50 (m, 5 H), 1.45-0.95 (m, 15H); MS: m/z 434 (M++1).

後処理

  1. temperatureThe reaction mixture is cooled to RT
  2. custompurified by chromatography on silica gel
  3. washgradient elution with heptane:EtOAc (70:30-50:50)

出典と根拠

ORDレコード
ord-77af2833d1c347c2b08d7641f38020e5
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

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