Triethylamine → 1-[1-(2-toluoylmethyl)-2-oxo-5-(3,3-dimethylbutanoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea

HRID 1979402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1979402
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:32]1([CH3:62])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53](=[O:59])[CH2:54][C:55]([CH3:58])([CH3:57])[CH3:56])[CH2:44][CH:43]([NH2:60])[C:42]2=[O:61])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>O1CCCC1.C(Cl)Cl.O>[C:32]1([CH3:62])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53](=[O:59])[CH2:54][C:55]([CH3:57])([CH3:58])[CH3:56])[CH2:44][CH:43]([NH:60][C:14]([NH:1][C:2]3[CH:12]=[CH:11][CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=3)=[O:16])[C:42]2=[O:61])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 212017651-(2-toluoylmethyl)-2-oxo-3-amino-5-(3,3-dimethylbutanoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 212015771-[1-(2-toluoylmethyl)-2-oxo-5-(3,3-dimethylbutanoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)ureaAusbeute 165,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Ethyl 3-aminobenzoate (236 mg) was dissolved in tetrahydrofuran (40 ml), under ice-cooling triphosgene (140 mg) was added and triethylamine (120 μl) was added thereto five times every 3 minutes, a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-(3,3-dimethylbutanoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (536 mg) in tetrahydrofuran (10 ml) was subsequently added, the mixture was stirred for 30 minutes at same temperature,and additionally stirred for 2 hours at room temperature. The reaction mixture was poured into water (400 ml),extracted with methylene chloride (50 ml), and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1), to thereby obtain 479 mg of the titled compound

Aufarbeitung

  1. additionwas added
  2. stirringadditionally stirred for 2 hours at room temperature
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-e605156c228e4ac69377375d34e8ad7d
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239131B1

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