1,1'-Carbonyldiimidazole → tert-butyl (S)-2-(3-(3-(2-(methoxycarbonylamino)ethoxy)-3-(3-chlorophenyl)propyl)-3-methylureido)-3-cyclohexylpropyl(methyl)carbamate

HRID 426071ノート

反応式

HRID 426071 の反応式
C1N=CN([C:6]([N:8]2[CH:12]=N[CH:10]=[CH:9]2)=[O:7])C=1.[NH2:13][C@@H:14]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].CCN(C(C)C)C(C)C.[Cl:41][C:42]1[CH:43]=[C:44]([CH:48]([O:53][CH2:54][CH2:55][NH:56][C:57](=[O:60])[O:58][CH3:59])CCNC)[CH:45]=[CH:46][CH:47]=1>C(Cl)Cl>[CH3:59][O:58][C:57]([NH:56][CH2:55][CH2:54][O:53][CH:48]([C:44]1[CH:45]=[CH:46][CH:47]=[C:42]([Cl:41])[CH:43]=1)[CH2:10][CH2:9][N:8]([CH3:12])[C:6](=[O:7])[NH:13][C@@H:14]([CH2:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)[CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:60]

参加物

6

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 59201313tert-butyl (S)-2-amino-3-cyclohexylpropylmethylcarbamateHCID 59364348Methyl 2-(1-(3-chlorophenyl)-3-(methylamino)propoxy)ethylcarbamate

生成物 1

HCID 86642388tert-butyl (S)-2-(3-(3-(2-(methoxycarbonylamino)ethoxy)-3-(3-chlorophenyl)propyl)-3-methylureido)-3-cyclohexylpropyl(methyl)carbamate収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

At 0° C., CDI (48.6 mg, 0.3 mmol) was added to a solution of (S)-tert-butyl 2-amino-3-cyclohexylpropyl(methyl)carbamate (81 mg, 0.3 mmol), prepared using procedures described in U.S. Prov. App No. 05/036,230 (PCT App No. 60/616,770), and DIEA (161 mg, 1.25 mmol) in anhydrous CH2Cl2 (8 mL) followed by stirring for 1 h. The solution was added to methyl 2-(1-(3-chlorophenyl)-3-(methylamino)propoxy)ethylcarbamate (75 mg, 0.25 mmol) in anhydrous CH2Cl2 (4 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. After the reaction was completed, the solvent was removed in vacuo. The product was purified with preparative TLC to afford tert-butyl (S)-2-(3-(3-(2-(methoxycarbonylamino)ethoxy)-3-(3-chlorophenyl)propyl)-3-methylureido)-3-cyclohexylpropyl(methyl)carbamate (70 mg, 50%).

後処理

  1. customprepared
  2. stirringstirred overnight
  3. customthe solvent was removed in vacuo
  4. customThe product was purified with preparative TLC

出典と根拠

ORDレコード
ord-bb1820f9a8324aaea13897e9d76d59b3
出典データセット
uspto-grants-2012_01
特許番号
US08106221B2

反応ノート

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