Acetic Acid → 1-(11-Acetoxy-12-bromododecyl)-3,7-dimethylxanthine

HRID 1954147ノート

反応式

HRID 1954147 の反応式
[OH:1][CH:2]([CH2:26]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:22](=[O:23])[C:21]2[N:20]([CH3:24])[CH:19]=[N:18][C:17]=2[N:16]([CH3:25])[C:14]1=[O:15].[BrH:28].O.[C:30]([OH:33])(=O)[CH3:31]>>[C:30]([O:1][CH:2]([CH2:26][Br:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:22](=[O:23])[C:21]2[N:20]([CH3:24])[CH:19]=[N:18][C:17]=2[N:16]([CH3:25])[C:14]1=[O:15])(=[O:33])[CH3:31]

参加物

5

反応物 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 234356281-(11,12-Dihydroxydodecyl)-3,7-dimethylxanthine

生成物 1

HCID 232959191-(11-Acetoxy-12-bromododecyl)-3,7-dimethylxanthine収率 99%

実験手順

1-(11,12-Dihydroxydodecyl)-3,7-dimethylxanthine (2.50 g, 6.58 mmol) was stirred with hydrogen bromide (6.39 mL of a 30% solution in acetic acid, 19.73 mmol) for 2 hours. The mixture was then added over 10 minutes to water (25 mL), ice (30 g) and sodium hydride CO3 (15 g) and stirred for 30 minutes. The reaction mixture was extracted with dichloromethane (3×50 mL), and the combined organic phases were dried using magnesium sulfate and evaporated to obtain 3.18 g (99% yield) of 1-(11-acetoxy-12-bromododecyl)-3,7-dimethylxanthine. Without further purification, this crude product was taken up in methanol (10 mL) and treated with a solution of sodium methoxide (prepared from sodium, 0.160 g, 6.90 mmol, and 20 mL methanol). After 60 minutes, the reaction was added to water (30 mL) and extracted with dichloromethane (3×50 mL). The organic portions were combined, dried and evaporated to yield 2.20 g (93% yield) 1-(11,12-oxidododecyl)-3,7-dimethylxanthine as a white solid.

後処理

  1. extractionThe reaction mixture was extracted with dichloromethane (3×50 mL)
  2. customthe combined organic phases were dried
  3. customevaporated

出典と根拠

ORDレコード
ord-92f26edde52646ceb6dca8f20a6ac348
出典データセット
uspto-grants-2000_09
特許番号
US06121270

反応ノート

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