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

HRID 1979418노트

반응식

HRID 1979418 반응식
[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]([C:55]3[O:56][CH:57]=[CH:58][CH:59]=3)=[O:54])[CH2:44][CH:43]([NH2:60])[C:42]2=[O:61])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>O1CCCC1>[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]([C:55]3[O:56][CH:57]=[CH:58][CH:59]=3)=[O:54])[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

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 212017961-(2-toluoylmethyl)-2-oxo-3-amino-5-(furan-2-ylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

생성물 1

HCID 212018391-[1-(2-toluoylmethyl)-2-oxo-5-(furan-2-ylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea수율 96.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Ethyl 3-aminobenzoate (373 mg) was dissolved in tetrahydrofuran (60 ml), under ice-cooling triphosgene (225 mg) was added, triethylamine (194 μl) was added thereto five times every 3 minutes, a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-(furan-2-ylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (856 mg) in tetrahydrofuran (15 ml) was added thereto, the mixture was allowed to come to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure, water (50 ml) was added to the residue, extracted with methylene chloride. The organic layer was 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 447 mg of the titled compound.

후처리

  1. additionwas added
  2. customto come to room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water (50 ml)
  4. additionwas added to the residue
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic layer was dried 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)

출처 및 근거

ORD 기록
ord-40d810fa8bf54af7aa12f45f6c23e3db
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239131B1

반응 노트

불러오는 중…