Sodium Hydroxide → 3-cyclopentyl-2-(4-methoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid

HRID 2381496Notes

Reaction equation

HRID 2381496 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH3:19])[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>CO>[CH:6]1([CH2:5][CH:4]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH3:19])[CH:13]=[N:12]2)[C:3]([OH:20])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 668752163-cyclopentyl-2-(4-methoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester

Product 1

HCID 668754403-cyclopentyl-2-(4-methoxy-6-oxo-6H-pyridazin-1-yl)-propionic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-methoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (458.8 mg, 1.63 mmol) in methanol (1.09 mL, 1.5M) was treated with a 4N aqueous sodium hydroxide solution (0.45 mL, 1.8 mmol) and was stirred at 25° C. overnight. At this time, the reaction was concentrated in vacuo. The residue was partitioned between water (100 mL), which was then acidified with a 2N aqueous hydrochloric acid solution to pH=2, and a 90/10 methylene chloride/methanol solution. The reaction was then extracted with a 90/10 methylene chloride/methanol solution (3×75 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(4-methoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid (430 mg, 98%) as a white solid; ES+-HRMS m/e calcd for C13H18N2O4 [M+Na+] 289.1159, found 289.1159. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.93-1.22 (m, 2H), 1.33-1.78 (m, 7H), 1.84-2.03 (m, 1H), 2.06-2.21 (m, 1H), 3.82 (s, 3H), 5.32 (dd, J=10.9, 3.9 Hz, 1H), 6.30 (d, J=2.7 Hz, 1H), 7.82 (d, J=2.7 Hz, 1H), 12.96 (br. s., 1H).

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. customThe residue was partitioned between water (100 mL), which
  3. extractionThe reaction was then extracted with a 90/10 methylene chloride/methanol solution (3×75 mL)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90614a616d4f41f29d3df04e3be4fccd
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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