Acetic Acid → 1-(4-(R)-methyl-7-acetoxy-8-bromo-8-methylnonyl)-3,7-dimethylxanthine

HRID 1954155노트

반응식

[CH3:1][C@@H:2]([CH2:19][CH2:20][CH:21]([OH:26])[C:22](O)([CH3:24])[CH3:23])[CH2:3][CH2:4][CH2:5][N:6]1[C:15](=[O:16])[C:14]2[N:13]([CH3:17])[CH:12]=[N:11][C:10]=2[N:9]([CH3:18])[C:7]1=[O:8].[BrH:27].O.C(=O)(O)[O-].[Na+].[C:34]([OH:37])(=O)[CH3:35]>>[CH3:1][C@@H:2]([CH2:19][CH2:20][CH:21]([O:26][C:34](=[O:37])[CH3:35])[C:22]([Br:27])([CH3:24])[CH3:23])[CH2:3][CH2:4][CH2:5][N:6]1[C:15](=[O:16])[C:14]2[N:13]([CH3:17])[CH:12]=[N:11][C:10]=2[N:9]([CH3:18])[C:7]1=[O:8]

참가 물질

반응물 5

HCID 176Acetic Acid

HCID 260Hydrogen Bromide

HCID 962Water

HCID 516892Sodium Bicarbonate

HCID 22941881HCID 22941881, 화합물

생성물 1

HCID 229418821-(4-(R)-methyl-7-acetoxy-8-bromo-8-methylnonyl)-3,7-dimethylxanthine

실험 절차

1-(4-(R)-Methyl-7,8-dihydroxy-8-methylnonyl)-3,7-dimethylxanthine (0.29 g, 0.80 mmol) was stirred with hydrogen bromide (1.00 mL of a 30% solution in acetic acid, 2.40 mmol) for 4 hours. The mixture was then added over 10 minutes to water (10 mL), ice (5 g) and sodium bicarbonate (2 g) and stirred for 30 minutes. The reaction mixture was extracted with dichloromethane (2×15 mL), the combined organic phases dried using magnesium sulfate and the solvent evaporated to obtain a residue of 1-(4-(R)-methyl-7-acetoxy-8-bromo-8-methylnonyl)-3,7-dimethylxanthine.

후처리

extractionThe reaction mixture was extracted with dichloromethane (2×15 mL)
customthe combined organic phases dried
customthe solvent evaporated

출처 및 근거

ORD 기록: ord-32b3a886f742494eb47cff3235a3c4d9
출처 데이터셋: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06121270

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