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

HRID 426071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426071
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bb1820f9a8324aaea13897e9d76d59b3
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106221B2

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