Lithium hydroxide, monohydrate → 2-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

HRID 714300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714300
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=3)[C:15]([O:17]C)=[O:16])[C:8]2=[O:22])=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=3)[C:15]([OH:17])=[O:16])[C:8]2=[O:22])=[CH:23][CH:24]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Produkt 1

HCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate (4.57 g, 13.90 mmol) and lithium hydroxide monohydrate (4.05 g, 96.52 mmol) in tetrahydrofuran (170 mL) and water (85 mL) was stirred for 19 hours. The organic solvent was removed in vacuo. The aqueous solution was acidified with 12 M hydrochloric acid solution until pH 3. The solid was filtered, washed with water (30 mL), hexanes (20 mL) and dried in vacuo to give 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid as a colorless solid (4.15 g, 95%). 1H NMR (300 MHz, DMSO-d6) δ 8.71 (s, 1H), 8.40 (d, J=5.1 Hz, 1H), 7.37-7.31 (m, 3H), 7.18-7.13 (m, 2H), 4.39 (s, 2H), 3.94 (t, J=8.1 Hz, 2H), 3.35 (t, J=8.1 Hz, 2H); MS (ES+) m/z 316.2 (M+1).

Aufarbeitung

  1. customThe organic solvent was removed in vacuo
  2. filtrationThe solid was filtered
  3. washwashed with water (30 mL), hexanes (20 mL)
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fe97cf8b8a20439ca132da7e12f9c130
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187426B2

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