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

HRID 1979396ノート

反応式

HRID 1979396 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([CH3:60])[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]([CH2:53][CH:54]=[C:55]([CH3:57])[CH3:56])[CH2:44][CH:43]([NH2:58])[C:42]2=[O:59])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>O1CCCC1>[C:32]1([CH3:60])[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]([CH2:53][CH:54]=[C:55]([CH3:56])[CH3:57])[CH2:44][CH:43]([NH:58][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:59])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 212019361-(2-toluoylmethyl)-2-oxo-3-amino-5-(3-methyl-2-butenyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

生成物 1

HCID 212018081-[1-(2-toluoylmethyl)-2-oxo-5-(3-methyl-2-butenyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea収率 120.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Ethyl 3-aminobenzoate (221 mg) was dissolved in tetrahydrofuran (20 ml), under ice-cooling triphosgene (134 mg) was added, triethylamine (115 μl) was added thereto five times every 3 minutes,a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-(3-methyl-2-butenyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (477 mg) in tetrahydrofuran (20 ml) was added dropwise thereto, and the mixture was stirred for 30 minutes at same temperature and subsequently stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, water (50 ml) was added, and extracted with methylene chloride. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(chloroform:ethyl acetate=10:1), to thereby obtain 316 mg of the titled compound.

後処理

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water (50 ml)
  3. additionwas added
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  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(chloroform:ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-dea02af5160f49c0ad70b682606662ce
出典データセット
uspto-grants-2001_05
特許番号
US06239131B1

反応ノート

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