Hydrochloric Acid → HCID 58739266、化合物

HRID 720624

反応式

HRID 720624 の反応式
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=3)[NH:10][C:9]=2[C:8](=[O:25])[NH:7][C:6]1=[O:26])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:34][O:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38].Cl>CN(C)C=O.O>[C:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:11]2[N:10]([CH2:34][O:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[C:9]3[C:8](=[O:25])[NH:7][C:6](=[O:26])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:13]=3[N:12]=2)=[CH:16][CH:17]=1)(=[O:24])[CH3:23]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 87885Chloromethyl pivalateHCID 21891817N-[4-(3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-acetamide

生成物 1

HCID 58739266HCID 58739266、化合物収率 41.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of N-[4-(3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-acetamide (196 mg, 0.55 mmol) in N,N-dimethylformamide (5.0 mL) at 25° C. was treated with sodium carbonate (117 mg, 0.55 mmol) and 2,2-dimethyl-propionic acid chloromethyl ester (0.10 mL, 0.55 mmol). The resulting mixture was warmed to 50° C. for 8 h. At this time, the reaction mixture was poured into a solution of water (2.5 mL) containing a 1N aqueous hydrochloric acid solution (1.65 mL). This solution was extracted with ethyl acetate. The organics were washed with water (1×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 3:2 ethyl acetate/petroleum ether) afforded 2,2-dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester (107 mg, 41.4%) as a yellow foam: FAB-HRMS m/e calcd for C24H31N5O5 (M+H)+ 470.2403, found 470.2408.

後処理

  1. extractionThis solution was extracted with ethyl acetate
  2. washThe organics were washed with water (1×100 mL)
  3. dry with materiala saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d1c05721873b41bb83b1dd2853ff9c11
出典データセット
uspto-grants-2006_11
特許番号
US07135475B2

関連ノート

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