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

HRID 352105노트

반응식

HRID 352105 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a8efe481e17d42438c85c8a6137a7583
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743939B2

반응 노트

불러오는 중…