Hydrochloric Acid → 3-(2-Hydroxyethyl)-5-(1,2,4-triazol-1-ylmethyl)-1h-indol-2-carboxylic acid methyl ester

HRID 1180099

반응식

HRID 1180099 반응식
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11]2[C:16](=[O:20])[O:17][CH2:18][CH2:19][C:10]3=2)[CH:5]=[N:4][CH:3]=[N:2]1.Cl.CS(O)(=O)=O.[CH3:27][OH:28]>>[CH3:27][O:28][C:16]([C:11]1[NH:12][C:13]2[C:9]([C:10]=1[CH2:19][CH2:18][OH:17])=[CH:8][C:7]([CH2:6][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)=[CH:15][CH:14]=2)=[O:20]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6395Methanesulfonic AcidHCID 104008226-(1,2,4-Triazol-1-ylmethyl)-4,9-dihydro-3h-pyrano[3,4-b]indol-1-on

생성물 1

HCID 116308013-(2-Hydroxyethyl)-5-(1,2,4-triazol-1-ylmethyl)-1h-indol-2-carboxylic acid methyl ester수율 94%

실험 절차

To a suspension of 2.5 g (8.2 mmoles) of the 6-(1,2,4-triazol-1-ylmethyl)-4,9-dihydro-3H-pyrano[3,4-b]indol-1-on a hydrochloride in 50 ml of methanol were added 0.66 ml (10.2 mmoles) of methanesulphonic acid. The mixture was left under stirring at the reflux temperature for 4 hours. The solvent was evaporated to dryness under reduced pressure, the residue dissolved with 10 ml of a saturated bicarbonate solution and extracted 3 times with ethyl acetate. The combined organic phases were dried and evaporated to dryness and the evaporated solid recrystallised from isopropyl alcohol/heptane to give 2.3 g (94%) of the title ester as a yellow crystalline solid.

후처리

  1. waitThe mixture was left
  2. customThe solvent was evaporated to dryness under reduced pressure
  3. dissolutionthe residue dissolved with 10 ml of a saturated bicarbonate solution
  4. extractionextracted 3 times with ethyl acetate
  5. customThe combined organic phases were dried
  6. customevaporated to dryness
  7. customthe evaporated solid recrystallised from isopropyl alcohol/heptane

출처 및 근거

ORD 기록
ord-7696ed5722304a4fb55c267a2688eea7
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279581B2

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