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

HRID 1979441노트

반응식

HRID 1979441 반응식
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(N(CC)CC)C.[C:32]([C:36]([CH2:38][N:39]1[C:45]2[CH:46]=[C:47]([CH3:50])[CH:48]=[CH:49][C:44]=2[N:43]([CH:51]2[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)[CH2:42][CH:41]([NH2:57])[C:40]1=[O:58])=[O:37])([CH3:35])([CH3:34])[CH3:33]>O1CCCC1>[C:32]([C:36]([CH2:38][N:39]1[C:45]2[CH:46]=[C:47]([CH3:50])[CH:48]=[CH:49][C:44]=2[N:43]([CH:51]2[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)[CH2:42][CH:41]([NH:57][C:2]([NH:13][C:14]2[CH:24]=[CH:23][CH:22]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=2)=[O:4])[C:40]1=[O:58])=[O:37])([CH3:35])([CH3:33])[CH3:34]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 212019271-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

생성물 1

HCID 212018501-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-ethoxycarbonylphenyl)urea수율 164.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Triphosgene (122 mg) was added to a solution of ethyl 3-aminobenzoate (182 mg) in tetrahydrofuran (10 ml) under ice-cooling, triethylamine (98 μl) was added thereto five times (total: 490 μl), the mixture was stirred at room temperature for 5 minutes. A solution of 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (393 mg) in anhydrous tetrahydrofuran (5 ml) was added to the mixture under ice-cooling, stirred at room temperature for 30 minutes. Ice-water was added to the reaction mixture, extracted with methylene chloride. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and a mixed solvent of n-hexane and ethyl acetate(n-hexane:ethyl acetate=1:1) was added to the residue for crystallization, collected by filtration, to thereby obtain 380 mg of the title compound.

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred at room temperature for 30 minutes
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additiona mixed solvent of n-hexane and ethyl acetate(n-hexane:ethyl acetate=1:1) was added to the residue for crystallization
  9. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-8d6990c42b9b4626981a9205ef4a6054
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239131B1

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