Acetic Acid → 3-(5-Acetoxy-6-bromohexyl)-1-methylthymine

HRID 356621노트

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HRID 356621 반응식
[OH:1][CH:2]([CH2:17]O)[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]([CH3:14])=[CH:10][N:9]([CH3:15])[C:8]1=[O:16].[BrH:19].[C:20]([OH:23])(=O)[CH3:21].C(=O)(O)[O-].[Na+]>ClCCl.O>[C:20]([O:1][CH:2]([CH2:17][Br:19])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]([CH3:14])=[CH:10][N:9]([CH3:15])[C:8]1=[O:16])(=[O:23])[CH3:21]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 232879373-(5,6-Dihydroxyhexyl)-1-methylthymine

생성물 1

HCID 232959113-(5-Acetoxy-6-bromohexyl)-1-methylthymine수율 100%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

3-(5,6-Dihydroxyhexyl)-1-methylthymine (1.65 g, 6.4 mmol) was stirred with 30% hydrogen bromide in acetic acid (3.8 ml, 19.3 mmol) for 1.5 hours. The mixture was then added to a mixture of sodium bicarbonate (6.7 g), water (40 ml), and dichloromethane (50 ml). After 15 minutes of vigorous stirring, the layers were separated and the aqueous layer was extracted with dichloromethane (2×50 ml). The combined organic layers were dried over sodium sulfate and the solvent was evaporated under vacuum to give 3-(5-acetoxy-6-bromohexyl)-1-methylthymine (2.30 g, 100% yield). The bromoacetate was used in the next step without further purification. 3-(5-Acetoxy-6-bromohexyl)-1-methylthymine (2.30 g, 6.4 mmol) was dissolved in methanol (10 ml) and a solution of 1M sodium methoxide in methanol (7 ml) was added. After stirring for 15 minutes, the solution was poured into water (60 ml) and extracted with 20% ethanol-dichloromethane (2×70 ml). The combined organic layers were dried over sodium sulfate and the solvents were evaporated under vacuum to give 3-(5,6-oxidohexyl)-1-methylthymine (1.30 g, 85% yield) as a white solid.

후처리

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (2×50 ml)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customthe solvent was evaporated under vacuum

출처 및 근거

ORD 기록
ord-1ef39d1fa63f45fea13ea8a365332c46
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05837703

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