Methyl butyrate → HCID 14978400, compound

HRID 1654227Notes

Reaction equation

HRID 1654227 reaction equation
[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.CCCC(OC)=O>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

Participants

6

Reactant 4

HCID 12180Methyl butyrateHCID 18050Methyl 3-mercaptopropionateHCID 113457231H-1,2,4-Triazole, 1-[[(2S,3S)-2-(2,4-difluorophenyl)-3-methyloxiranyl]methyl]-HCID 23694274Sodium methanolate methanol2×

Product 1

HCID 14978400HCID 14978400, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (25 ml) were dissolved (2S,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane (1.0 g), methyl 3-mercaptopropionate (3.5 ml) and 28% sodium methoxide-methanol (3.07 g) and the solution was refluxed in an oil bath. After 2 and after 3 hours, methyl 3-methylpropionate (1.75 ml) and 28% sodium methoxide-methanol (1.5 g) were added at each time. The oil bath was removed after heating for 4 hours and the reaction mixture was neutralized with cold 1N hydrochloric acid (32 ml) and extracted with dichloromethane (200 ml). The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium 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 recrystallized from ethyl acetate-hexane to give (2S,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1 H-1,2,4-triazol-1-yl)-2-butanol (compound 117, 472 mg) as colorless needles.

Workup

  1. temperaturethe solution was refluxed in an oil bath
  2. customThe oil bath was removed
  3. temperatureafter heating for 4 hours
  4. extractionextracted with dichloromethane (200 ml)
  5. washThe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: hexane-ethyl acetate=1:3)
  9. concentrationThe desired fraction was concentrated
  10. customthe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9d6e9f68e2a54cd98ac56c5e3b4e81c4
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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