Hydrochloric Acid → 2-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

HRID 273770

반응식

HRID 273770 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+].C[O-].[Na+].CO.Cl>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

7

반응물 5

HCID 313Hydrochloric AcidHCID 18050Methyl 3-mercaptopropionate2회HCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 10942334Sodium MethoxideHCID 23694274Sodium methanolate methanol

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

A solution of (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 methylate methanolic solution (1.25 ml) in methanol (10 ml) was refluxed for 4.5 hours in an oil bath under heating. To the reaction mixture was added methyl 3-mercaptopropionate (0.53 ml, 0.32 ml) respectively after 2 hours and 3.5 hours of heating. Further, 28% sodium methylate-methanol solution (0.63 ml) was added after 2.5 hours. After 4.5 hours, 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 saline (20 ml), dried over anhydrous sodium sulfate and distilled off the solvent under reduced pressure. The residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=1:3) for purification. The objective fractions were concentrated. Then, the collected precipitate was washed with isopropyl ether to afford (2R, 3R)-2-(2,4-difluorophenyl )-3-mercapto-1-(1-H-1,2,4-triazol-1-yl)-2-butanol (0.22 g) as colorless needles.

후처리

  1. temperatureunder heating
  2. temperature3.5 hours of heating
  3. temperaturethe reaction mixture was cooled
  4. extractionextracted with dichloromethane (100 ml)
  5. washThe extract was washed with saturated saline (20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled off the solvent under reduced pressure
  8. customThe residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=1:3) for purification
  9. concentrationThe objective fractions were concentrated
  10. washThen, the collected precipitate was washed with isopropyl ether

출처 및 근거

ORD 기록
ord-7ea57d3faa75457cb75dcb9354a662fa
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387599

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