Oxalic Acid → 4-Chloro-2-[[(1R)-4-(methylamino)-1-phenylbutyl]oxy]benzonitrile ethanedioate

HRID 352105ノート

反応式

HRID 352105 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]I)[CH:3]=1.[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[CH3:28][NH2:29]>O1CCCC1.CO>[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][NH:29][CH3:28])[CH:3]=1

参加物

6

反応物 3

HCID 971Oxalic AcidHCID 6329MethylamineHCID 698282664-Chloro-2-[[(1r)-4-iodo-1-phenylbutyl]oxy]benzonitrile

生成物 1

HCID 865883464-Chloro-2-[[(1R)-4-(methylamino)-1-phenylbutyl]oxy]benzonitrile ethanedioate

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of the product from step (c) (286 mg) in 40% aqueous methylamine (1 ml) and tetrahydrofuran (10 ml) was stirred for 6 h. The solvent was removed in vacuo and the residue dissolved in water and extracted with ethyl acetate (three times). The combined organic extracts were washed with water, dried (magnesium sulphate) and evaporated to give an oil. To a solution of this amine in methanol (10 ml) was added a solution of oxalic acid (57 mg) in methanol. The solvent was removed in vacuo and the residue triturated with ethyl acetate. The solid was collected and dried to afford the title compound as a white solid (110 mg). M.p. 167-169° C.

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with ethyl acetate (three times)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customto give an oil
  8. customThe solvent was removed in vacuo
  9. customthe residue triturated with ethyl acetate
  10. customThe solid was collected
  11. customdried

出典と根拠

ORDレコード
ord-a8efe481e17d42438c85c8a6137a7583
出典データセット
uspto-grants-2004_06
特許番号
US06743939B2

反応ノート

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