Water → 9-(2-Acetoxyethoxymethyl)guanine

HRID 865354

反応式

HRID 865354 の反応式
[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].C[Si](C)(C)N[Si](C)(C)C.C(O[CH2:25][O:26][CH2:27][CH2:28][O:29][C:30](=[O:32])[CH3:31])(=O)C.O>CC(C)=O.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>[C:30]([O:29][CH2:28][CH2:27][O:26][CH2:25][N:6]1[CH:7]=[N:8][C:9]2[C:10](=[O:11])[NH:1][C:2]([NH2:3])=[N:4][C:5]1=2)(=[O:32])[CH3:31]

参加物

7

反応物 4

HCID 962WaterHCID 13838HexamethyldisilazaneHCID 1009992-((Acetyloxy)methoxy)ethyl acetateHCID 135398634Guanine

生成物 1

HCID 1354469309-(2-Acetoxyethoxymethyl)guanine収率 58%

試薬・触媒・溶媒 2

HCID 6097028Ammonium Sulfate触媒HCID 180Acetone溶媒

反応条件

温度
130 °C

実験手順

A mixture of 10 gms (66 mmoles) of guanine, 50 ml of hexamethyldisilazane, and 0.4 gms (3 mmmol) of ammonium sulfate was heated to 115°-118° C. for 18 hours. The ammonia gas was removed as it was formed. After 18 hours of heating, a solution was formed indicating the completion of silylation. To this solution was added 15 gms (85 mmol) of 2-oxa-1,4-butanediol diacetate and 0.1 ml of trimethylsilyl triftriflate. The mixture was heated to 130° C. for a period of 4.5 hours. The solution was cooled to 50° C. and 10 ml of water dissolved in 100 ml of acetone was added. The mixture was heated to reflux and a precipitate was formed immediately. The mixture was cooled and the solid was collected by filtration to yield 10.1 g (58% yield) of 9-(2-acetoxyethoxy)methylguanine, with a 13:1 ratio of N-9 to N-7 isomer. Characteristic analytical data are as follows: 1H NMR (DMSO-d6) δ1.90 (3H, singlet, --OAc) , 3.58 (2H, multiplet, --OCH2 --) , 4.0 (2H, multiplet, --CH2OAc) , 5.25 (2H, singlet, --NCH2O--), 6.5 (2H, br singlet, --NH2), 7.75 (1H, singlet, --N=CH--N--).

後処理

  1. temperaturewas heated to 115°-118° C. for 18 hours
  2. customThe ammonia gas was removed as it
  3. customwas formed
  4. temperatureAfter 18 hours of heating
  5. customa solution was formed
  6. temperatureThe solution was cooled to 50° C.
  7. additionwas added
  8. temperatureThe mixture was heated
  9. temperatureto reflux
  10. customa precipitate was formed immediately
  11. temperatureThe mixture was cooled
  12. filtrationthe solid was collected by filtration

出典と根拠

ORDレコード
ord-f22f74916a7141e4a0b366c9d9269572
出典データセット
uspto-grants-1996_10
特許番号
US05565565

関連ノート

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