Theobromine → 1-(7-Octenyl)-3,7-dimethylxanthine

HRID 1379014

反応式

HRID 1379014 の反応式
O[CH:2]([CH2:22]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11].[H-].[Na+].N1C(=O)C2N(C)C=NC=2N(C)C1=O.BrCCCCCCC=C>CS(C)=O.O>[CH2:8]([N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:22]

参加物

7

反応物 4

HCID 5429TheobromineHCID 24758Sodium hydrideHCID 759078-Bromooct-1-eneHCID 97973341-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine

生成物 1

HCID 152306341-(7-Octenyl)-3,7-dimethylxanthine収率 97%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

1-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine (CT1538) was used as an intermediate for the synthesis of CT1514 (example 15). To a suspension of sodium hydride (580 mg, 24.2 mmol) in dimethylsulfoxide (100 ml) was added theobromine (3.96 g, 22.0 mmol). After stirring for 30 min, 8-bromo-1-octene (3.96 g, 22 mmol) was added and the mixture was stirred for 16 hr. The mixture was poured into water (200 ml) and extracted with dichloromethane (3×50 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 ml), dried over sodium sulfate, and the solvent was evaporated under vacuum to give 1-(7-octenyl)-3,7-dimethylxanthine (CT1535) (6.22 g, 97% yield) as an oil which solidified upon standing.

後処理

  1. stirringthe mixture was stirred for 16 hr
  2. extractionextracted with dichloromethane (3×50 ml)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (50 ml)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under vacuum

出典と根拠

ORDレコード
ord-2ce3bf41138e4b8a90a20bc9fcac6066
出典データセット
uspto-grants-1997_09
特許番号
US05670506

関連ノート

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