Triphosgene → 1-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonyl-4-methylphenyl)urea

HRID 1979481노트

반응식

HRID 1979481 반응식
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][C:14]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[C:28]([C:32]([CH2:34][N:35]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]([CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)[CH2:38][CH:37]([NH2:52])[C:36]1=[O:53])=[O:33])([CH3:31])([CH3:30])[CH3:29]>O1CCCC1.C(N(CC)CC)C>[C:28]([C:32]([CH2:34][N:35]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]([CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)[CH2:38][CH:37]([NH:52][C:2]([NH:27][C:24]2[CH:25]=[CH:26][C:14]([CH3:13])=[C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH:23]=2)=[O:4])[C:36]1=[O:53])=[O:33])([CH3:31])([CH3:29])[CH3:30]

참가 물질

6

반응물 3

HCID 94429TriphosgeneHCID 154908351-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineHCID 21202027Tert-butyl 5-amino-2-methylbenzoate

생성물 1

HCID 212018351-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonyl-4-methylphenyl)urea수율 235.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매

실험 절차

Under ice-cooling, triphosgene (205 mg) was added to a solution of tert-butyl 2-methyl-5-aminobenzoate (383 mg) in anhydrous tetrahydrofuran (40 ml), triethylamine (825 μl) was added thereto five times over 15 minutes after divided into five portions. After the mixture was stirred at room temperature for 5 minutes, a solution of 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (600 mg) in anhydrous tetrahydrofuran (10 ml) was added under ice-cooling. The resultant mixture was stirred at room temperature for one hour, the reaction mixture was poured into ice-water, extracted with ethyl acetate, and the organic layer was washed with saturated brine. After dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, diisopropyl ether was added to the residue for crystallization, and collected by filtration, to thereby obtain 960 mg of the title compound (Yield: 97%).

후처리

  1. temperatureUnder ice-cooling
  2. additionwas added
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialAfter dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure, diisopropyl ether
  8. additionwas added to the residue for crystallization
  9. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-aefa23a3a8ae4605bf18f15024b64618
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239131B1

반응 노트

불러오는 중…