Diisopropylethylamine → 8-(3'-Benzyloxybiphenyl-4-ylmethyl-amino)-2',3',5'-tris-o-(tert-butyldimethylsilyl)adenosine

HRID 1713296노트

반응식

HRID 1713296 반응식
Br[C:2]1[N:3]([C:34]2[N:35]=[CH:36][N:37]=[C:38]([NH2:41])[C:39]=2[N:40]=1)[C@@H:4]1[O:33][C@H:23]([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C@@H:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C@H:5]1[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[CH2:42]([O:49][C:50]1[CH:51]=[C:52]([C:56]2[CH:61]=[CH:60][C:59]([CH2:62][NH2:63])=[CH:58][CH:57]=2)[CH:53]=[CH:54][CH:55]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(N(CC)C(C)C)(C)C>C(O)CC>[CH2:42]([O:49][C:50]1[CH:51]=[C:52]([C:56]2[CH:57]=[CH:58][C:59]([CH2:62][NH:63][C:2]3[N:3]([C:34]4[N:35]=[CH:36][N:37]=[C:38]([NH2:41])[C:39]=4[N:40]=3)[C@@H:4]3[O:33][C@H:23]([CH2:24][O:25][Si:26]([C:29]([CH3:30])([CH3:31])[CH3:32])([CH3:28])[CH3:27])[C@@H:14]([O:15][Si:16]([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:18])[CH3:17])[C@H:5]3[O:6][Si:7]([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:9])[CH3:8])=[CH:60][CH:61]=2)[CH:53]=[CH:54][CH:55]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 109304658-Bromo-2',3',5'-tris-o-(tert-butyl-dimethylsilyl)adenosineHCID 230050193'-Benzyloxybiphenyl-4-ylmethylamine

생성물 1

HCID 674544418-(3'-Benzyloxybiphenyl-4-ylmethyl-amino)-2',3',5'-tris-o-(tert-butyldimethylsilyl)adenosine수율 83.3%

시약·촉매·용매 1

HCID 10311-Propanol용매

실험 절차

A mixture of 8-bromo-2′,3′,5′-tris-O-(tert-butyl-dimethylsilyl)adenosine (0.660 g), 3′-benzyloxybiphenyl-4-ylmethylamine (0.832 g) and N,N-diisopropylethylamine (0.667 mL) in 1-propanol (9.6 mL) was heated under reflux with stirring for 62 hours. The reaction mixture was cooled to room temperature and then partitioned between ethyl acetate (35 mL) and 10% aqueous citric acid (10 mL). The organic layer was washed successively with 10% aqueous citric acid (10 mL×2), saturated aqueous sodium hydrogen carbonate (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on aminopropylated silica gel (eluent: hexane/ethyl acetate=2/1) to give the title compound (0.716 g).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux
  3. custompartitioned between ethyl acetate (35 mL) and 10% aqueous citric acid (10 mL)
  4. washThe organic layer was washed successively with 10% aqueous citric acid (10 mL×2), saturated aqueous sodium hydrogen carbonate (10 mL) and brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on aminopropylated silica gel (eluent: hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-a0b63de5fdc2456f988d2280abfbcb6d
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795236B2

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