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

HRID 2381394Notes

Reaction equation

C[O:2][C:3](=[O:19])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([I:18])[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([I:18])[CH:13]=[N:12]2)[C:3]([OH:19])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (Intermediate 73, Step 2, 1.78 g, 4.73 mmol) in tetrahydrofuran (13 mL, 0.36M) was treated with a 4N aqueous sodium hydroxide solution (1.3 mL, 5.2 mmol) and stirred at 25° C. overnight. After this time, the reaction was concentrated in vacuo and the residue was diluted with water (50 mL) and was then acidified with a 1N aqueous hydrochloric acid solution. The precipitate was filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid (1.45 g, 85%) as an off-white solid; ES+-HRMS m/e calcd for C12H15N2O3I [M+H+] 363.0200, found 363.0197. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95-1.18 (m, 2H), 1.36-1.75 (m, 7H), 1.88-2.02 (m, 1H), 2.17 (ddd, J=13.9, 10.8, 5.1 Hz, 1H), 5.30 (dd, J=10.8, 4.3 Hz, 1H), 7.65 (d, J=1.9 Hz, 1H), 8.23 (d, J=1.9 Hz, 1H), 13.10 (s, 1H).

Workup

concentrationAfter this time, the reaction was concentrated in vacuo
additionthe residue was diluted with water (50 mL)
filtrationThe precipitate was filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-cb9b2a4a220e4c368bc08f26bbf7d9c6
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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