Acetic Acid → 3-(8-Acetoxy-9-bromononyl)-1-methylthymine

HRID 1954138ノート

反応式

HRID 1954138 の反応式
[OH:1][CH:2]([CH2:20]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19].[BrH:22].[C:23]([OH:26])(=O)[CH3:24].C(=O)(O)[O-].[Na+]>ClCCl>[C:23]([O:1][CH:2]([CH2:20][Br:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19])(=[O:26])[CH3:24]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 232879543-(8,9-Dihydroxynonyl)-1-methylthymine

生成物 1

HCID 232959773-(8-Acetoxy-9-bromononyl)-1-methylthymine収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-(8,9-dihydroxynonyl)-1-methylthymine (2.16 g, 7.6 mmol) and a 30% solution of hydrogen bromide in acetic acid (4.5 mL, 23 mmol) was stirred for 1 hour. The reaction was added slowly to a beaker containing sodium bicarbonate (8.4 g, 0.1 mol), ice water (30 mL), and dichloromethane (30 mL). The layers were separated and the aqueous layer extracted with dichloromethane (2×60 mL). The combined organic layers were washed with water (30 mL), saturated aqueous salt solution (30 mL), and dried over sodium sulfate. The solvent was removed to yield 2.59 g (85% yield) 3-(8-acetoxy-9-bromononyl)-1-methylthymine (inventive compound no. 1908) as a thick, slightly orange oil.

後処理

  1. additionThe reaction was added slowly to a beaker
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane (2×60 mL)
  4. washThe combined organic layers were washed with water (30 mL), saturated aqueous salt solution (30 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed

出典と根拠

ORDレコード
ord-512efbae1c57448da2ede4acd503f5af
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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