Pyridine → 5'-O-(2-(2-chloro-6-nitrophenyl)ethoxycarbonyl)-N6-(2-(4-nitrophenyl)ethoxycarbonyl)-2'-deoxyadenosine

HRID 963772

反応式

HRID 963772 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][C:13]([NH:15][C:16]2[C:17]3[N:18]=[CH:19][N:20]([C:29]=3[N:30]=[CH:31][N:32]=2)[C@@H:21]2[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[CH2:22]2)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[Cl:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([N+:46]([O-:48])=[O:47])[C:41]=1[CH2:49][CH2:50][O:51][C:52](Cl)=[O:53].CC(O)C.N#N>C(Cl)Cl>[Cl:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([N+:46]([O-:48])=[O:47])[C:41]=1[CH2:49][CH2:50][O:51][C:52]([O:27][CH2:26][C@H:25]1[O:28][C@@H:21]([N:20]2[C:29]3[N:30]=[CH:31][N:32]=[C:16]([NH:15][C:13]([O:12][CH2:11][CH2:10][C:7]4[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)=[O:14])[C:17]=3[N:18]=[CH:19]2)[CH2:22][C@@H:23]1[OH:24])=[O:53]

参加物

6

反応物 4

HCID 1049PyridineHCID 10873933Adenosine, 2'-deoxy-N-[[2-(4-nitrophenyl)ethoxy]carbonyl]-HCID 190826922-(2-Chloro-6-nitrophenyl)ethoxycarbonyl chlorideHCID 86752769N2 isopropanol

生成物 1

HCID 152893455'-O-(2-(2-chloro-6-nitrophenyl)ethoxycarbonyl)-N6-(2-(4-nitrophenyl)ethoxycarbonyl)-2'-deoxyadenosine収率 83.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-60 °C

実験手順

N6 -(2-(4-nitrophenyl)ethoxycarbonyl)-2'-deoxyadenosine (5 g, 11.3 mmol) was co-evaporated with pyridine (2×60 ml, pro analysi quality, additionally dried over molecular sieve 4 Å), dissolved in pyridine (60 ml, see above) and cooled to -60° C. (i-PrOH/N2). A solution of 2-(2-chloro-6-nitrophenyl)ethoxycarbonyl chloride (4.17 g, 15.8 mmol) in CH2Cl2 (60 ml, dist. over CaH2) was added dropwise for 2 h. After it had been stirred another 2 h in conditions of i-PrOH/N2 cooling (-40° to -25° C.), the mixture was diluted with CH2Cl2 (150 ml) and washed with H2O (100 ml). The aqueous phases were post-extracted with CH2Cl2 (100 ml). Drying the organic phases over Na2SO4, filtering, evaporating the solvent under reduced pressure and co-evaporating with toluene (3×50 ml) yielded the crude product (8.73 g) which was purified by column chromatography (400 g SiO2, 28×5.7 cm, solvent: CH2Cl2 /MeOH 100:3). 5'-O-(2-(2-chloro-6-nitrophenyl)ethoxycarbonyl)-N6 -(2-(4-nitrophenyl)ethoxycarbonyl)-2'-deoxyadenosine (6.318 g, 83%) was obtained as a colourless foam.

後処理

  1. customadditionally dried over molecular sieve 4 Å),
  2. dissolutiondissolved in pyridine (60 ml, see above)
  3. washwashed with H2O (100 ml)
  4. extractionThe aqueous phases were post-extracted with CH2Cl2 (100 ml)
  5. dry with materialDrying the organic phases over Na2SO4
  6. filtrationfiltering
  7. customevaporating the solvent under reduced pressure and co-evaporating with toluene (3×50 ml)
  8. customyielded the crude product (8.73 g) which
  9. customwas purified by column chromatography (400 g SiO2, 28×5.7 cm, solvent: CH2Cl2 /MeOH 100:3)

出典と根拠

ORDレコード
ord-b955e8564b194225b07b6f47b790838d
出典データセット
uspto-grants-1998_06
特許番号
US05763599

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