Phosphoric Acid → HCID 14978401, compound

HRID 1654219Notes

Reaction equation

HRID 1654219 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.P(=O)(O)(O)O>CO.O>[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

7

Reactant 4

HCID 1004Phosphoric AcidHCID 18050Methyl 3-mercaptopropionate2×HCID 113797241-(((2S,3R)-2-(2,4-difluorophenyl)-3-Methyloxiran-2-yl)Methyl)-1H-1,2,4-triazoleHCID 23694274Sodium methanolate methanol2×

Product 1

HCID 14978401HCID 14978401, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of (2S,3R)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane (30 mg), methyl 3-mercaptopropionate (0.09 ml) and 28% sodium methoxide-methanol (0.08 ml) in methanol (2 ml) was refluxed for 2 hours, after which 28% sodium methoxide-methanol (0.04 ml) was added and the mixture was refluxed for another hour. Then, methyl 3-mercaptopropionate (0.04 ml) was added and the mixture was further refluxed for 2 hours. The reaction mixture was cooled, diluted with water (2 ml), neutralized with 5% aqueous phosphoric acid solution and extracted with methylene chloride (3 ml×2). The extract was dried over anhydrus sodium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (1×5 cm) using ethyl acetate-hexane (3:1) as the eluent. The desired fraction was concentrated and the residue was crystallized from ethyl acetate-isopropyl ether to give (2S,3S)-2-(2,4-difluorophenyl)-3-mercapto- 1-(1H-1,2,4-triazol-1-yl)-2-butanol (compound 42:11 mg) as colorless prisms.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturethe mixture was refluxed for another hour
  3. temperaturethe mixture was further refluxed for 2 hours
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with methylene chloride (3 ml×2)
  6. dry with materialThe extract was dried over anhydrus sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. concentrationThe desired fraction was concentrated
  9. customthe residue was crystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-440c050fc3fa40578fcb59eefbc3caec
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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