tert-Butyl piperazine-1-carboxylate → 4-[1,3-Bis(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1792058노트

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HRID 1792058 반응식
Cl[C:2]1[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:9]2[C:8](=[O:16])[N:7]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C:6](=[O:25])[N:5]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:4]=2[N:3]=1.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].C12CCCCC1CCCNN=2>CN1CCCC1=O>[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][N:44]([C:2]2[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:9]3[C:8](=[O:16])[N:7]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:22])[CH3:23])[C:6](=[O:25])[N:5]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:4]=3[N:3]=2)[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]

참가 물질

5

반응물 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 235368912,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl esterHCID 66879275Diazabicyclo[5.4.0]undecene

생성물 1

HCID 235369414-[1,3-Bis(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester수율 45%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
150 °C

실험 절차

2,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (470 mg) and 1-piperazinecarboxylic acid tert-butyl ester (218 mg) were dissolved in N-methylpyrrolidone (4 ml), and diazabicyclo[5.4.0]undecene (160 μl) was added to the solution. The mixture was stirred at 150° C. for 6.5 hours. The reaction mixture was filtered through Celite, diluted with chloroform, washed with water, and dried over anhydrous magnesium sulfate. After the solvent was removed by distillation from the organic layer, the residue was purified by silica gel column chromatography to give 277 mg of the title compound from the elution fraction of hexane-ethyl acetate (2:1)

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. additiondiluted with chloroform
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was removed by distillation from the organic layer
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-467d5e98194d49c9a3f7f03f8527eb1c
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074798B2

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