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

HRID 361533노트

반응식

HRID 361533 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-0804e91a238b45659ce961967e27d6fd
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866576

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