Methyl 3-mercaptopropionate → 2-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

HRID 1654220노트

반응식

HRID 1654220 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])[O:10]1.[SH:19]CCC(OC)=O.C[O-].[Na+].CO>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:10])([C@H:11]([SH:19])[CH3:12])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1

참가 물질

5

반응물 3

HCID 18050Methyl 3-mercaptopropionate2회HCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 23694274Sodium methanolate methanol2회

생성물 1

HCID 1922642-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

In methanol (10 ml) were dissolved (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane (0.40 g), methyl 3-mercaptopropionate (1.42 ml) and 28% sodium methoxide-methanol (1.25 ml) and the solution was refluxed. After 2 and after 3.5 hours, (0.53 ml and 0.32 ml each of) methyl 3-mercaptopropionate were added, and after 2.5 minutes, 28% sodium methoxide-methanol (0.63 ml) was added. At 4.5 hours after the beginning of heating, the oil bath was removed and the reaction mixture was cooled, neutralized with 1N hydrochloric acid (9.6 ml) and extracted with dichloromethane (100 ml). The extract was washed with saturated aqueous sodium chloride solution (20 ml) and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: hexane-ethyl acetate=1:3). The desired fraction was concentrated and the resulting crystals were collected and washed with isopropyl ether to give (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol (compound 43:0.22 g) as colorless needles. m.p. 176°-178° C.

후처리

  1. temperaturethe solution was refluxed
  2. waitafter 2.5 minutes
  3. temperatureAt 4.5 hours after the beginning of heating
  4. customthe oil bath was removed
  5. temperaturethe reaction mixture was cooled
  6. extractionextracted with dichloromethane (100 ml)
  7. washThe extract was washed with saturated aqueous sodium chloride solution (20 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel chromatography (eluent: hexane-ethyl acetate=1:3)
  11. concentrationThe desired fraction was concentrated
  12. customthe resulting crystals were collected
  13. washwashed with isopropyl ether

출처 및 근거

ORD 기록
ord-c980c4bfb49941019ca5e8423bfd753e
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05405861

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