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

HRID 2381492Notes

Reaction equation

C[O:2][C:3](=[O:18])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[CH:14][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]=[CH:14][CH:13]=[N:12]2)[C:3]([OH:18])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (2.99 g, 11.97 mmol) in methanol (7.9 mL, 1.5M) was treated with a 4N aqueous sodium hydroxide solution (3.29 mL, 13.16 mmol) and stirred at 25° C. overnight. At this time, the reaction was concentrated in vacuo. The residue was partitioned between water (100 mL) which was acidified with a 2N aqueous hydrochloric acid solution and a solution of 90/10 methylene chloride/methanol (3×75 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid (2.45 g, 86%) as a light pink solid; ES+-HRMS m/e calcd for C12H16N2O3 [M+H+] 237.1234, found 237.1233.

Workup

concentrationAt this time, the reaction was concentrated in vacuo
customThe residue was partitioned between water (100 mL) which
dry with materialThe combined organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d2bed4eec58a40439f699d01e13acb2a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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