Triethylamine → ({2-[(2,6-Dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoyl}oxy)methyl pivalate

HRID 1869810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869810
[Cl:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:3]=1[C:4]([NH:6][CH:7]([CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])[CH:16]=[CH:15]2)[C:8]([OH:10])=[O:9])=[O:5].C(N(CC)CC)C.[C:42]([O:48][CH2:49]Cl)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44]>CCOC(C)=O>[C:42]([O:48][CH2:49][O:9][C:8](=[O:10])[CH:7]([NH:6][C:4](=[O:5])[C:3]1[C:30]([Cl:34])=[CH:31][CH:32]=[CH:33][C:2]=1[Cl:1])[CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])[CH:16]=[CH:15]2)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 10052832N-(2,6-dichlorobenzoyl)-3-[2-(2,6-dichlorophenyl)-6-quinolyl]alanine

Produkt 1

HCID 57987629({2-[(2,6-Dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoyl}oxy)methyl pivalateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoic acid 38 (534 mg) are added 195 μl of triethylamine and, after 15 minutes, 290 μl of chloromethyl pivalate. The solution is stirred at RT overnight and then poured in AcOEt. The organic phases are washed with water and brine, dried over MgSO4 and concentrated. The resulting residue is purified over silica gel using CH2Cl2/C2H5OH 99/1 as eluent to give ({2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoyl}oxy)methyl pivalate 129.

Aufarbeitung

  1. washThe organic phases are washed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe resulting residue is purified over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b0b5ff02a90742fca93e1d136be04b99
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638630B2

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