Benzyl Alcohol → 2-Amino-6-Benzyloxy-9-Carboxymethylpurine

HRID 50092

反応式

HRID 50092 の反応式
[Na].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][C:13]([OH:15])=[O:14])=[C:5](Cl)[N:4]=1.[OH-].[Na+].[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][C:13]([OH:15])=[O:14])=[C:5]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:4]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 14798Sodium HydroxideHCID 41928332-Amino-6-chloro-9H-purine-9-acetic acidHCID 5360545Sodium

生成物 1

HCID 100633112-Amino-6-Benzyloxy-9-Carboxymethylpurine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

Sodium (2.0 g; 87.0 mmol) was dissolved in benzyl alcohol (20 ml) and heated to 130° C. for 2 h. After cooling to 0° C., a solution of 2-amino-6-chloro-9-carboxymethylpurine (4.05 g; 18.0 mmol) in DMF (85 ml) was slowly added, and the resulting suspension stirred overnight at 20° C. Sodium hydroxide solution (1N, 100 ml) was added and the clear solution was washed with ethyl acetate (3×100 ml). The water phase then was acidified to a pH of 3 with 4 N hydrochloric acid. The precipitate was taken up in ethyl acetate (200 ml), and the water phase was extracted with ethyl acetate (2×100 ml). The combined organic phases were washed with saturated sodium chloride solution (2×75 ml), dried with anhydrous sodium sulfate, and taken to dryness by evaporation, in vacuo. The residue was recrystallized from ethanol (300 ml). Yield after drying, in vacou, over sicapent: 2.76 g (52%). M.p. 159-65° C. Anal. (calc., found) C(56.18; 55.97); H(4.38; 4.32); N(23.4; 23.10). 1H-NMR (DMSO-d6): 4.82 ppm.(s,2H); 5.51 (s,2H); 6.45 (s,2H); 7.45 (m,5H); 7.82 (s,1H).

後処理

  1. temperatureAfter cooling to 0° C.
  2. washthe clear solution was washed with ethyl acetate (3×100 ml)
  3. extractionthe water phase was extracted with ethyl acetate (2×100 ml)
  4. washThe combined organic phases were washed with saturated sodium chloride solution (2×75 ml)
  5. dry with materialdried with anhydrous sodium sulfate
  6. customtaken to dryness by evaporation, in vacuo
  7. customThe residue was recrystallized from ethanol (300 ml)
  8. customYield
  9. customafter drying, in vacou

出典と根拠

ORDレコード
ord-0f1d0e7ba78641d88257a635a96fcfa4
出典データセット
uspto-grants-2004_03
特許番号
US06710163B1

関連ノート

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