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 1979396노트

반응식

HRID 1979396 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([CH3:60])[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

참가 물질

6

반응물 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

생성물 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)urea수율 120.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dea02af5160f49c0ad70b682606662ce
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239131B1

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