Potassium Iodide → 3-[3-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid

HRID 1979483노트

반응식

HRID 1979483 반응식
C(OC(=O)CBr)(C)(C)C.[C:10]([O:14][C:15]([CH2:17][N:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:21][CH:20]([NH:35][C:36]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([O:47]CC3C=CC=CC=3)=[O:46])[CH:40]=2)=[O:37])[C:19]1=[O:55])=[O:16])([CH3:13])([CH3:12])[CH3:11].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].O=C1NC2C=CC=CC=2N(C2CCCCC2)CC1NC(NC1C=CC=C(C(OCC2C=CC=CC=2)=O)C=1)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[C:10]([O:14][C:15]([CH2:17][N:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:21][CH:20]([NH:35][C:36](=[O:37])[NH:38][C:39]2[CH:40]=[C:41]([CH:42]=[CH:43][CH:44]=2)[C:45]([OH:47])=[O:46])[C:19]1=[O:55])=[O:16])([CH3:13])([CH3:11])[CH3:12]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 212017761-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea Tert-butyl bromoacetateHCID 212018741-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea

생성물 1

HCID 212019863-[3-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid수율 295.3%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

Preparation of 1-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea Tert-butyl bromoacetate (503 mg), potassium iodide (23 ml), tetra n-butylammonium bromide (23 mg) and potassium carbonate (713 mg) were added to a solution of 1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea (800 mg) in dimethylsulfoxide (10 ml), the mixture was stirred at room temperature for one hour. Ice-water was added thereto, 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 970 mg of the titled compound (Yield: 90%).

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-781f2416c743401180355aaede82e3e7
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239131B1

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