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

HRID 1979431
ノート
印刷プレビュー

反応式

HRID 1979431 の反応式
[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([CH3:61])[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]([CH:53]3[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]3)[CH2:44][CH:43]([NH2:59])[C:42]2=[O:60])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>O1CCCC1.O>[C:32]1([CH3:61])[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]([CH:53]3[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58]3)[CH2:44][CH:43]([NH:59][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:60])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 212018461-(2-toluoylmethyl)-2-oxo-3-amino-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

生成物 1

HCID 212015691-[1-(2-toluoylmethyl)-2-oxo-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea収率 202.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Ethyl 3-aminobenzoate (100 mg) was dissolved in tetrahydrofuran (5 ml), the solution was cooled on ice, triphosgene (65 mg) was added thereto at internal temperature 5° C., triethylamine (220 mg) was added thereto at 3 minutes intervals, the mixture was allowed to come to room temperature and stirred for 10 minutes. A solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (820 mg) in tetrahydrofuran (5 ml) was added, additionally stirred for one hour. Water was added to the reaction mixture, extracted with methylene chloride. The organic layer was successively washed with water and saturated brine, 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=3:1), to thereby obtain 265 mg of the titled compound (Yield 81%).

後処理

  1. additionwas added
  2. customto come to room temperature
  3. stirringadditionally stirred for one hour
  4. extractionextracted with methylene chloride
  5. washThe organic layer was successively washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-fc023937dd14415dae35dcb85717ae73
出典データセット
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06239131B1

反応ノート

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