Pyridine → 5'-O-(2-(2-chloro-6-nitrophenyl)ethoxycarbonyl)-N4-(2-(4-nitrophenyl)ethoxycarbonyl)-2'-deoxycytidine

HRID 963771

反応式

HRID 963771 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[CH:29]=[CH:28][N:19]([C@@H:20]3[O:27][C@H:24]([CH2:25][OH:26])[C@@H:22]([OH:23])[CH2:21]3)[C:18](=[O:30])[N:17]=2)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[Cl:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([N+:44]([O-:46])=[O:45])[C:39]=1[CH2:47][CH2:48][O:49][C:50](Cl)=[O:51].CC(O)C.N#N>C(Cl)Cl>[Cl:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([N+:44]([O-:46])=[O:45])[C:39]=1[CH2:47][CH2:48][O:49][C:50]([O:26][CH2:25][C@H:24]1[O:27][C@@H:20]([N:19]2[CH:28]=[CH:29][C:16]([NH:15][C:13]([O:12][CH2:11][CH2:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)=[O:14])=[N:17][C:18]2=[O:30])[CH2:21][C@@H:22]1[OH:23])=[O:51]

参加物

6

反応物 4

HCID 1049PyridineHCID 153824852'-Deoxy-N-{[2-(4-nitrophenyl)ethoxy]carbonyl}cytidineHCID 190826922-(2-Chloro-6-nitrophenyl)ethoxycarbonyl chlorideHCID 86752769N2 isopropanol

生成物 1

HCID 544564125'-O-(2-(2-chloro-6-nitrophenyl)ethoxycarbonyl)-N4-(2-(4-nitrophenyl)ethoxycarbonyl)-2'-deoxycytidine収率 680%

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

N4 -(2-(4-nitrophenyl)ethoxycarbonyl)-2'-deoxycytidine (5 g, 11.9 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 (4.7 g, 17.8 mmol) in CH2Cl2 (60 ml, dist. over CaH2) was added dropwise thereto for 75 min and was stirred for 1 h 45 min 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 (9.8 g) which was purified by column chromatography (440 g SiO2, 32×5.9 cm, solvent: CH2Cl2 /MeOH 100:4). 5'-O-(2-(2-chloro-6-nitrophenyl)ethoxycarbonyl)-N4 -(2-(4-nitrophenyl)ethoxycarbonyl)-2'-deoxycytidine (5.247 g, 680%) 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 (9.8 g) which
  9. customwas purified by column chromatography (440 g SiO2, 32×5.9 cm, solvent: CH2Cl2 /MeOH 100:4)

出典と根拠

ORDレコード
ord-9615d9b765264c8cb6f5b0a1a99b2403
出典データセット
uspto-grants-1998_06
特許番号
US05763599

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