Potassium Carbonate → (R)-(-)-1-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea

HRID 1979467노트

반응식

HRID 1979467 반응식
Br[CH2:2][C:3]([C:5]([CH3:8])([CH3:7])[CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].[O:15]=[C:16]1[NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:18][C@H:17]1[NH:33][C:34]([NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH:38]=1)=[O:35]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.[I-].[K+]>[C:5]([C:3]([CH2:2][N:22]1[C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[CH2:18][C@@H:17]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44])[CH:38]=2)=[O:35])[C:16]1=[O:15])=[O:4])([CH3:8])([CH3:7])[CH3:6]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 54084555(R)-(-)-1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea

생성물 1

HCID 53986084(R)-(-)-1-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea수율 95%

시약·촉매·용매 3

HCID 4875Potassium Iodide촉매HCID 74236Tetrabutylammonium Bromide촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

Bromomethyl tert-butylketone (2.95 g), potassium iodide (125 mg), tetra n-butylammonium bromide (145 mg) and potassium carbonate (2.07 g) were added to a solution of (R)-(−)-1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea (7.18 g) in dimethylsulfoxide (100ml), the mixture was stirred for 2hours at room temperature. The reaction mixture was poured into ice-water, extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:2), to thereby obtain 8.22 g of the titled compound (Yield 95%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:2)

출처 및 근거

ORD 기록
ord-2e787b1846044463b4064a03af12920b
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239131B1

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