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

HRID 426071노트

반응식

HRID 426071 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-bb1820f9a8324aaea13897e9d76d59b3
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106221B2

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