Acetic Acid → Methyl alpha-(3-Trifluoromethylphenylmethylamino)-5-methoxy-3-indoleacetate

HRID 5612

반응식

HRID 5612 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].[C:13]([OH:16])(=[O:15])[CH3:14].O.[C:18](O)(=O)C=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=[CH:28]2>CO>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[C:5]([CH2:6][NH:7][CH:14]([C:28]2[C:27]3[C:31](=[CH:32][CH:33]=[C:25]([O:24][CH3:23])[CH:26]=3)[NH:30][CH:29]=2)[C:13]([O:16][CH3:18])=[O:15])[CH:8]=[CH:9][CH:10]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 138725-MethoxyindoleHCID 759623-(Trifluoromethyl)benzylamineHCID 15620607Glyoxylic acid, monohydrate

생성물 1

HCID 19796684Methyl alpha-(3-Trifluoromethylphenylmethylamino)-5-methoxy-3-indoleacetate

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a stirred solution of 7.24 g (41.34 mmoles) of 3-(trifluoromethyl)benzylamine and 4 mL (4.2 g, 69.88 mmoles) of acetic acid in 50 mL of MeOH was added a solution of 3.65 g (41.34 mmoles) of glyoxylic acid monohydrate in 50 mL of MeOH followed by 5.07 g (34.45 mmoles) of 5-methoxyindole. The resulting solution was allowed to stand for three days. Solid separated during this period. The solid was collected by filtration, washed with MeOH, and dried giving 3.02 g f white solid, m.p. ca. 192° C. (dec). The solvent was evaporated from the combined filtrate and washing. The residue was treated with 200 mL of H2O. Sodium bicarbonate was added until the CO2 evolution ceased. The mixture was extracted with CH2Cl2 (3×100 mL). The combined extracts were washed with 50 mL of brine and dried over MgSO4. Evaporation of the solvent left 8.71 g of brown oil with slowly solidified. The solid was chromatographed on a 700 g column of silica gel. The column was eluted with 30% acetone-Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel TLC (1×4") (40% acetone-Skellysolve B). Fractions 14-20 were combined and crystallized from CH2Cl2 -hexane giving 5.14 g of ivory-buff solid. The solid was recrystallized from acetone-hexane giving 4.8 g (36%) of the title compound as ivory needles, m.p. 109°-110.5° C.

후처리

  1. customSolid separated during this period
  2. filtrationThe solid was collected by filtration
  3. washwashed with MeOH
  4. customdried
  5. customgiving 3.02 g f white solid, m.p. ca. 192° C. (dec)
  6. customThe solvent was evaporated from the combined filtrate
  7. washwashing
  8. additionThe residue was treated with 200 mL of H2O
  9. additionSodium bicarbonate was added until the CO2 evolution
  10. extractionThe mixture was extracted with CH2Cl2 (3×100 mL)
  11. washThe combined extracts were washed with 50 mL of brine
  12. dry with materialdried over MgSO4
  13. customEvaporation of the solvent
  14. waitleft 8.71 g of brown oil with slowly solidified
  15. customThe solid was chromatographed on a 700 g column of silica gel
  16. washThe column was eluted with 30% acetone-Skellysolve B and 200 mL fractions
  17. customwere collected
  18. customcrystallized from CH2Cl2 -hexane giving 5.14 g of ivory-buff solid
  19. customThe solid was recrystallized from acetone-hexane giving 4.8 g (36%) of the title compound as ivory needles, m.p. 109°-110.5° C.

출처 및 근거

ORD 기록
ord-2ab8d445b07a4216a285e80f012a3dfa
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245046

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