Acetic Acid → 1-(8-Acetoxy-9-bromononyl)-3,7-dimethylxanthine

HRID 129881

反応式

HRID 129881 の反応式
[OH:1][CH:2]([CH2:23]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12].[BrH:25].[C:26]([OH:29])(=O)[CH3:27].C(=O)(O)[O-].[Na+]>ClCCl.O>[C:26]([O:1][CH:2]([CH2:23][Br:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12])(=[O:29])[CH3:27]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 98408081-(8,9-Dihydroxynonyl)-3,7-dimethylxanthine

生成物 1

HCID 153385971-(8-Acetoxy-9-bromononyl)-3,7-dimethylxanthine収率 96%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (428 mg, 1.3 mmol) and 30% hydrogen bromide in acetic acid (0.8 ml, 3.9 mmol) was stirred for 90 minutes. The solution was poured into a mixture of water (10 ml), sodium bicarbonate (1.35 g), and dichloromethane (10 ml). After 10 minutes of vigorous stirring the layers were separated and the aqueous portion was extracted with dichloromethane (3×15 ml). The combined organic phases were dried over sodium sulfate and the solvent was evaporated under vacuum to give 1-(8-acetoxy-9-bromononyl)-3,7-dimethylxanthine (550 mg, 96% yield) as a yellow oil. Without further purification, the oil was dissolved in methanol (5 ml) and then a 1M solution of sodium methoxide in methanol (1.4 ml) was added. After 30 minutes the reaction mixture was poured into water (30 ml) and extracted with dichloromethane (3×40 ml). The combined organic phases were dried over sodium sulfate and the solvents evaporated under vacuum. The solid residue was recrystallized (dichloromethane-petroleum ether) to give 1-(8,9-oxidononyl)-3,7-dimethylxanthine (380 mg, 91% yield).

後処理

  1. stirringAfter 10 minutes of vigorous stirring the layers
  2. customwere separated
  3. extractionthe aqueous portion was extracted with dichloromethane (3×15 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customthe solvent was evaporated under vacuum

出典と根拠

ORDレコード
ord-90e883bca33d486aaae47fda1cfacd71
出典データセット
uspto-grants-1995_11
特許番号
US05470878

関連ノート

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