Methanol → 3-cyclopentyl-2-(4-hydroxy-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester

HRID 2381398Notes

Reaction equation

HRID 2381398 reaction equation
[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([OH:18])[CH:13]=[N:12]2)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[CH3:23]O>>[CH3:23][O:9][C:8](=[O:10])[CH:7]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([OH:18])[CH:13]=[N:12]1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 668753163-cyclopentyl-2-(4-hydroxy-6-oxo-6H-pyridazin-1-yl)-propionic acid

Product 1

HCID 668754303-cyclopentyl-2-(4-hydroxy-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl esterYield 80%

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-hydroxy-6-oxo-6H-pyridazin-1-yl)-propionic acid (12.5 g, 47.6 mmol) in methanol (150 mL) was treated dropwise with thionyl chloride (7.1 g, 59.5 mmol). The mixture was stirred at reflux for 1 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. The resulting residue was partitioned between water and ethyl acetate. The combined organics were dried over sodium sulfate and concentrated in vacuo to afford 3-cyclopentyl-2-(4-hydroxy-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester as a light yellow oil (10.5 g, 80%).

Workup

  1. temperatureat reflux for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was partitioned between water and ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71b1f37d94f147ba8eb957fafaf91aa0
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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