Potassium Hydroxide → HCID 54393095, compound

HRID 362441Notes

Reaction equation

HRID 362441 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]([OH:25])([CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)[CH:12]([CH3:18])[CH2:13][S:14]C(=O)C>CO>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C@@:11]([OH:25])([CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)[C@@H:12]([CH3:18])[CH2:13][SH:14]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86753721HCID 86753721, compound

Product 1

HCID 54393095HCID 54393095, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under nitrogen atmosphere at room temperature a solution of potassium hydroxide (0.266 g; 4,74 mmoles) in methanol (40 ml) was dropped into a solution of thioacetic acid S-[3-(2.4-dichlorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyl] ester, prepared as described in Example 6 (1.72 g; 4.6 mmoles) in methanol (40 ml). After reacting for 10 minutes the reaction was quenched with 5% HCl (4 ml) diluted with water (20 ml), and the reaction mixture was concentrated under reduced pressure, then further diluted with water and extracted more times with methylene chloride. The anhydrification and evaporation of the collected organic phases yielded 1.6 g of a crude which was purified by flash chromatography of silica gel (eluent ethyl acetate:hexane=1:1). There was thus obtained 1.2 g (80%) of (2R,3R)-3-(2,4-dichlorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-1-butanthiol as a light oil.

Workup

  1. customprepared
  2. customthe reaction was quenched with 5% HCl (4 ml)
  3. additiondiluted with water (20 ml)
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionfurther diluted with water
  6. extractionextracted more times with methylene chloride
  7. customThe anhydrification and evaporation of the collected organic phases
  8. customyielded 1.6 g of a crude which
  9. customwas purified by flash chromatography of silica gel (eluent ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-c9883d12096340aba326a5fd49ebc703
Source dataset
uspto-grants-1999_02
Patent number
US05869512

Reaction notes

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