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 1979467ノート

反応式

HRID 1979467 の反応式
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]

参加物

7

反応物 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

生成物 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)urea収率 95%

試薬・触媒・溶媒 3

HCID 4875Potassium Iodide触媒HCID 74236Tetrabutylammonium Bromide触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-2e787b1846044463b4064a03af12920b
出典データセット
uspto-grants-2001_05
特許番号
US06239131B1

反応ノート

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