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

HRID 714300노트

반응식

HRID 714300 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fe97cf8b8a20439ca132da7e12f9c130
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187426B2

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