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

HRID 129881

반응식

HRID 129881 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-90e883bca33d486aaae47fda1cfacd71
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470878

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