Sodium Hydroxide → HCID 66875217, compound

HRID 2381359Notes

Reaction equation

C[O:2][C:3](=[O:27])[CH:4]([N:12]1[C:17](=[O:18])[C:16]([Cl:19])=[C:15]([O:20][CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:14]=[N:13]1)[CH2:5][CH:6]([CH2:10][CH3:11])[CH2:7][CH2:8][CH3:9].[OH-].[Na+]>CO>[Cl:19][C:16]1[C:17](=[O:18])[N:12]([CH:4]([CH2:5][CH:6]([CH2:10][CH3:11])[CH2:7][CH2:8][CH3:9])[C:3]([OH:27])=[O:2])[N:13]=[CH:14][C:15]=1[O:20][CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(5-chloro-4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-4-ethyl-heptanoic acid methyl ester (341.7 mg, 0.89 mmol) in methanol (0.6 mL, 1.49M) was treated with a 4N aqueous sodium hydroxide solution (0.24 mL, 0.98 mmol) and stirred at 25° C. for 3.5 h. After this time, the reaction was concentrated in vacuo. The residue was diluted with water (20 mL) and acidified with a 1N aqueous hydrochloric acid solution. The resulting gummy solids were collected by filtration, rinsed with water and dried in vacuo to afford 2-(5-chloro-4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-4-ethyl-heptanoic acid (296.1 mg, 90%) as a tacky, white solid; ES+-HRMS m/e calcd for C18H25N2O4Cl [M+H+] 369.1576, found 369.1575. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96-1.19 (m, 2H), 1.28-1.84 (m, 15H), 1.91-2.03 (m, 1H), 2.15-2.27 (m, 1H), 2.27-2.38 (m, 1H), 4.26 (d, J=6.8 Hz, 2H), 5.37 (dd, J=11.0, 4.2 Hz, 1H), 8.32 (s, 1H), 13.10 (br s, 1H).

Workup

concentrationAfter this time, the reaction was concentrated in vacuo
additionThe residue was diluted with water (20 mL)
filtrationThe resulting gummy solids were collected by filtration
washrinsed with water
customdried in vacuo

Sources & evidence

ORD record: ord-07a0c99a2bb145e89e5c7c8ab543c49a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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