Hydrochloric Acid → 3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-benzyl)-6H-pyridazin-1-yl]-propionic acid

HRID 2381364Notes

Reaction equation

C[O:2][C:3](=[O:29])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:27])[F:26])[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].O.Cl>CO.C(Cl)Cl.CO>[CH:6]1([CH2:5][CH:4]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:27])([F:28])[F:26])[CH:13]=[N:12]2)[C:3]([OH:29])=[O:2])[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-benzyl)-6H-pyridazin-1-yl]-propionic acid methyl ester (149.4 mg, 0.36 mmol) in methanol (0.61 mL, 0.6M) was treated with a 4N aqueous sodium hydroxide solution (0.1 mL, 0.40 mmol) and stirred at 25° C. for 3 h. After this time, the reaction was poured into water (50 mL) and 90/10 methylene chloride/methanol (30 mL) and was acidified with a 2N aqueous hydrochloric acid solution and then was extracted into a 90/10 methylene chloride/methanol (3×30 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-benzyl)-6H-pyridazin-1-yl]-propionic acid (130.6 mg, 90%) as a yellow solid. This material was used without further purification; ES+-HRMS m/e calcd for C20H21N2O3F3 [M+H+] 395.1577, found 395.1574.

Workup

extractionwas extracted into a 90/10 methylene chloride/methanol (3×30 mL)
dry with materialThe combined organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c84dff4d8df94381ade3491936196449
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

Loading…