Hydrochloric Acid → methyl 2-(3-ethoxy-5-ethyl-2-fluorophenyl)-2-hydroxyacetimidate HCl salt

HRID 1438160Notes

Reaction equation

[CH2:1]([O:3][C:4]1[C:5]([F:16])=[C:6]([CH:12]([OH:15])[C:13]#[N:14])[CH:7]=[C:8]([CH2:10][CH3:11])[CH:9]=1)[CH3:2].[CH3:17][OH:18].[ClH:19]>C(OCC)C.O1CCOCC1>[ClH:19].[CH2:1]([O:3][C:4]1[C:5]([F:16])=[C:6]([CH:12]([OH:15])[C:13](=[NH:14])[O:18][CH3:17])[CH:7]=[C:8]([CH2:10][CH3:11])[CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To 118E (630 mg, 2.93 mmol) in anhydrous diethyl ether (10 mL) at 0° C. was added MeOH (1.2 mL) and 4.0 N HCl in dioxane (2.9 mL). The mixture was stirred at 0° C. for 30 min and then at rt over night. Solvent was removed to give methyl 2-(3-ethoxy-5-ethyl-2-fluorophenyl)-2-hydroxyacetimidate HCl salt. To this salt in CH2Cl2 (5.0 mL) was added H2O (8.0 mL). The mixture was stirred at rt for 30 min, then extracted with CH2Cl2 (2×50 mL). The combined organic extracts were dried and concentrated. The crude was purified by column chromatography to give 118F (632 mg, 89% yield) as a viscous oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.20 (t, J=7.69 Hz, 3H) 1.43 (t, J=7.03 Hz, 3H) 2.58 (q, J=7.76 Hz, 2H) 3.76 (s, 3H) 4.04-4.13 (m, 2H) 5.37 (s, 1H) 6.68-6.81 (m, 2H).

Workup

waitat rt over night
customSolvent was removed

Sources & evidence

ORD record: ord-cd6138472c0d4e83bc47b1844f93d6eb
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622585B2

Reaction notes

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