Hydrochloric Acid → HCID 46223054, compound

HRID 2381305Notes

Reaction equation

C[O:2][C:3](=[O:25])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].O.Cl>CO>[CH:6]1([CH2:5][CH:4]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=[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-4-phenoxy-6H-pyridazin-1-yl)-propionic acid methyl ester (1.70 g, 4.96 mmol) in methanol (8.3 mL, 0.6M) was treated with a 4N aqueous sodium hydroxide solution (1.37 mL, 5.46 mmol) and was stirred at 25° C. for 4 h. After this time, the reaction was poured into water (150 mL) which was acidified with a 3N aqueous hydrochloric acid solution and then was extracted into 90/10 methylene chloride/methanol (3×100 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-propionic acid (1.60 g, 98%) as a white solid; ES+-HRMS m/e calcd for C18H20N2O4 [M+H+] 329.1496, found 329.2496. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.11 (br s, 2H), 1.35-1.78 (m, 7H), 1.86-2.05 (m, 1H), 2.10-2.25 (m, 1H), 5.31 (dd, J=10.9, 4.2 Hz, 1H), 5.73 (d, J=2.7 Hz, 1H), 7.30 (d, J=7.5 Hz, 2H), 7.37 (t, J=7.5 Hz, 1H), 7.53 (t, J=7.5 Hz, 2H), 8.10 (d, J=2.7 Hz, 1H), 13.02 (br s, 1H).

Workup

extractionwas extracted into 90/10 methylene chloride/methanol (3×100 mL)
dry with materialThe combined organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-de358bb4965d433993e26210e5bd4432
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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