Trimethylsilyl triflate → HCID 137010181、化合物

HRID 2205177ノート

反応式

HRID 2205177 の反応式
[O:1]=[C:2]1[NH:10][C:9]([NH:11][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[N:8][C:7]2[NH:6][CH:5]=[N:4][C:3]1=2.C(O[CH:21]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:24]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@:23]([CH2:41][O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([CH:38]([F:40])[F:39])[O:22]1)(=O)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.C([O-])(O)=O.[Na+]>CC#N>[C:27]([O:26][C@@H:25]1[C@H:24]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@:23]([CH2:41][O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([CH:38]([F:39])[F:40])[O:22][C@H:21]1[N:6]1[CH:5]=[N:4][C:3]2[C:2](=[O:1])[NH:10][C:9]([NH:11][C:12](=[O:16])[CH:13]([CH3:14])[CH3:15])=[N:8][C:7]1=2)(=[O:29])[CH3:28]

参加物

6

反応物 4

HCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 131735802HCID 131735802、化合物HCID 178454493HCID 178454493、化合物

生成物 1

HCID 137010181HCID 137010181、化合物収率 62%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
25 °C

実験手順

To a solution of compound N-(6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide (0.57 g, 2.58 mmol) in anhydrous CH3CN (50 mL) was added BSA (1.26 mL, 5.17 mmol) portion-wise while maintaining the reaction temperature at 25° C. Then the reaction was stirred at 40° C. for 1 h until a clear solution persisted. Compound 5 (0.6 g, 1.29 mmol) in CH3CN (5 mL) was added into the mixture at 0° C. followed by TMSOTf (0.94 mL, 5.17 mmol). The mixture was stirred at 40° C. for 2 h and then poured into saturated NaHCO3 solution (10 mL) at 0° C., extracted with ethyl acetate, washed with water, brine solution, dried over Na2SO4 and evaporated to dryness under reduced pressure. The crude compound was purified by silica gel chromatography [petroleum ether:ethyl acetate (5:1 to 1:1)] to provide the product 21 as a white foam (0.5 g, 60%). LC-MS: (M+H)+=626

後処理

  1. stirringThe mixture was stirred at 40° C. for 2 h
  2. extractionextracted with ethyl acetate
  3. washwashed with water, brine solution
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness under reduced pressure
  6. customThe crude compound was purified by silica gel chromatography [petroleum ether:ethyl acetate (5:1 to 1:1)]

出典と根拠

ORDレコード
ord-372499770dc44153b91264f3c6e14510
出典データセット
uspto-grants-2016_06
特許番号
US09370569B2

反応ノート

読み込み中…