Oxalic Acid → 4-Chloro-2-[[(1R)-1-phenyl-4-(1-pyrrolidinyl)butyl]oxy]-benzonitrile ethanedioate

HRID 352106노트

반응식

HRID 352106 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.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29]>O1CCCC1.C(O)(C)C.CO>[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29].[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][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:3]=1

참가 물질

7

반응물 3

HCID 971Oxalic AcidHCID 31268PyrrolidineHCID 698282664-Chloro-2-[[(1r)-4-iodo-1-phenylbutyl]oxy]benzonitrile

생성물 1

HCID 865883454-Chloro-2-[[(1R)-1-phenyl-4-(1-pyrrolidinyl)butyl]oxy]-benzonitrile ethanedioate

시약·촉매·용매 3

HCID 887Methanol용매HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of the product from Example 1 step (c) (200 mg) and pyrrolidine (0.15 ml) in tetrahydrofuran (5 ml) was stirred for 2 days. The solvent was removed in vacuo and the residue dissolved in water and aqueous potassium carbonate and extracted with ethyl acetate (three times). The combined organic extracts were washed with water, dried (Na2SO4) and evaporated to give an oil. To a solution of this amine in isopropanol (3 ml) was added a solution of oxalic acid (44 mg) in methanol (0.3 ml). The crystals that formed on cooling were collected and dried to afford the title compound as a white solid (163 mg). M.p. 157-158° C.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water
  3. extractionaqueous potassium carbonate and extracted with ethyl acetate (three times)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give an oil
  8. customThe crystals that formed
  9. temperatureon cooling
  10. customwere collected
  11. customdried

출처 및 근거

ORD 기록
ord-22dcac02f6cb45b6988975761f1eac57
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743939B2

반응 노트

불러오는 중…