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

HRID 2381357Notes

Reaction equation

HRID 2381357 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:19][CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[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][CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:13]=[N:12]2)[C:3]([OH:25])=[O:2])[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 668748313-cyclopentyl-2-(4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester

Product 1

HCID 579192473-cyclopentyl-2-(4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-propionic acidYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (702.6 g, 2.01 mmol) in methanol (1.3 mL, 1.55M) was treated with a 4N aqueous sodium hydroxide solution (0.55 mL, 2.22 mmol) and stirred at 25° C. overnight. After this time, the reaction was concentrated in vacuo. The resulting solids were then taken up in water (30 mL) and a 1N aqueous sodium hydroxide solution (20 mL) and extracted with methylene chloride (1×30 mL). The aqueous layer was then acidified with a 3N aqueous hydrochloric acid solution. The resulting precipitate was collected by filtration and dried in vacuo. The initial organics were treated with a 1N aqueous sodium hydroxide solution (50 mL), concentrated in vacuo, and then acidified with a 3N aqueous hydrochloric acid solution. The resulting precipitate was collected by filtration and dried in vacuo. The combined solids afforded 3-cyclopentyl-2-(4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid (490.5 mg, 73%) as a white solid; ES+-HRMS m/e calcd for C18H26N2O4 [M+H+] 335.1966, found 335.1964. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95-1.18 (m, 2H), 1.24-1.82 (m, 15H), 1.94 (ddd, J=13.6, 9.0, 4.0 Hz, 1H), 2.16 (ddd, J=13.8, 11.1, 5.1 Hz, 1H), 2.25-2.36 (m, 1H), 3.90 (d, J=7.0 Hz, 2H), 5.31 (dd, J=11.1, 4.0 Hz, 1H), 6.29 (d, J=2.8 Hz, 1H), 7.81 (d, J=2.8 Hz, 1H), 12.92 (br s, 1H).

Workup

  1. concentrationAfter this time, the reaction was concentrated in vacuo
  2. extractiona 1N aqueous sodium hydroxide solution (20 mL) and extracted with methylene chloride (1×30 mL)
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried in vacuo
  5. additionThe initial organics were treated with a 1N aqueous sodium hydroxide solution (50 mL)
  6. concentrationconcentrated in vacuo
  7. filtrationThe resulting precipitate was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-7c2eb07846d245738c2bac8b86ad0c31
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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