Triethylamine → N-1-Azabicyclo[2.2.2]oct-3-yl-2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]acetamide, monohydrochloride

HRID 5502

反応式

HRID 5502 の反応式
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([NH:10][C:11](=[O:14])[CH2:12][Cl:13])[CH2:3]2.[CH3:15][C:16]([C:19]1[CH:24]=[C:23]([SH:25])[CH:22]=[C:21]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]=1[OH:30])([CH3:18])[CH3:17].C(N(CC)CC)C>C(#N)C>[ClH:13].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([NH:10][C:11](=[O:14])[CH2:12][S:25][C:23]1[CH:22]=[C:21]([C:26]([CH3:27])([CH3:28])[CH3:29])[C:20]([OH:30])=[C:19]([C:16]([CH3:18])([CH3:17])[CH3:15])[CH:24]=1)[CH2:3]2

参加物

5

反応物 3

HCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 131716900N-1-Azabicyclo[2.2.2]oct-3-yl-2-chloroacetamide, monohydrochloride

生成物 1

HCID 131716901N-1-Azabicyclo[2.2.2]oct-3-yl-2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]acetamide, monohydrochloride

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

The title compound was prepared by dissolving the product of Example 17 (2.0 g, 0.0084 mole) and 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (1.99 g, 0.0084 mole) in acetonitrile (25 ml). Triethylamine (5 ml) was added to the mixture and the mixture stirred at room temperature for 12 hours then refluxed for 72 hours. The hot mixture was filtered and the solvent removed on a rotary evaporator. The residue was triturated with hexane and dissolved in hot ethyl acetate and allowed to cool. After filtering, the solvent was removed by a rotary evaporator and the residue recrystallized from ethyl acetate-methanol-ethyl ether to give a tan solid. The structure was confirmed by mass spectroscopy M+ 404.

後処理

  1. temperaturethen refluxed for 72 hours
  2. filtrationThe hot mixture was filtered
  3. customthe solvent removed on a rotary evaporator
  4. customThe residue was triturated with hexane
  5. dissolutiondissolved in hot ethyl acetate
  6. temperatureto cool
  7. filtrationAfter filtering
  8. customthe solvent was removed by a rotary evaporator
  9. customthe residue recrystallized from ethyl acetate-methanol-ethyl ether
  10. customto give a tan solid

出典と根拠

ORDレコード
ord-7c6e013327b6432ebdbce4d8fc732f65
出典データセット
uspto-grants-1993_09
特許番号
US05244899

関連ノート

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