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

HRID 2381507Notes

Reaction equation

C[O:2][C:3](=[O:25])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[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][C:13]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:12]2)[C:3]([OH:25])=[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-3-phenoxy-6H-pyridazin-1-yl)-propionic acid methyl ester (1.03 g, 3.03 mmol) in methanol (8.5 mL, 0.36M) was treated with a 4N aqueous sodium hydroxide solution (0.83 mL, 3.34 mmol) and stirred at 25° C. overnight. After this time, the reaction was concentrated in vacuo. The residue was diluted with water (100 mL) and acidified to pH=1 with a 3N aqueous hydrochloric acid solution. The resulting solids were collected by filtration, rinsed with water, air dried and then further dried in vacuo to afford 3-cyclopentyl-2-(6-oxo-3-phenoxy-6H-pyridazin-1-yl)-propionic acid (0.81 g, 81%) as a white solid. 1H-NMR (300 MHz, DMSO-d6) δ ppm 0.94 (br s, 2H), 1.29-1.70 (m, 7H), 1.79 (br s, 1H), 1.85-2.05 (m, 1H), 5.08 (dd, J=10.6, 3.0 Hz, 1H), 7.06 (d, J=9.7 Hz, 1H), 7.10-7.25 (m, 3H), 7.34-7.45 (m, 3H).

Workup

concentrationAfter this time, the reaction was concentrated in vacuo
additionThe residue was diluted with water (100 mL)
filtrationThe resulting solids were collected by filtration
washrinsed with water, air
customdried
customfurther dried in vacuo

Sources & evidence

ORD record: ord-cc3fff2746064936a38fea84fd580870
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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