Lithium Hydroxide → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid

HRID 1760666노트

반응식

HRID 1760666 반응식
C[O:2][C:3](=[O:27])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[O:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26].[OH-].[Li+]>O1CCOCC1.O>[CH2:12]([CH:11]([NH:10][C:9]1[C:4]([C:3]([OH:27])=[O:2])=[C:5]([O:17][C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:6]=[C:7]([CH3:16])[CH:8]=1)[CH2:14][CH3:15])[CH3:13]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 232165764-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester

생성물 1

HCID 218433964-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid수율 45.7%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester (16 mg, 0.043 mmol) and lithium hydroxide (30 mg) in dioxane (1 ml) and water (1 ml) was stirred at rt over night. The mixture was quenched with water and adjusted to pH 7.0 and extracted with chloroform. The organic layer was dried and concentrated to give the crude material. The crude material was purified through silica gel column chromatography using 10% ethyl acetate in chloroform as eluent to give 7 mg of the title compound as white solid. 1H NMR (CDCl3) δ 9.12 (d, 11H), 6.87 (s, 2H), 6.16 (s, 1H), 3.35 (m, 11H), 2.29 (s, 3H), 2.10 (s, 3H), 2.07 (s, 6H), 1.4-1.6 (m, 4H), 0.94 (t, 6H) ppm.

후처리

  1. customThe mixture was quenched with water
  2. extractionextracted with chloroform
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give the crude material
  6. customThe crude material was purified through silica gel column chromatography

출처 및 근거

ORD 기록
ord-85ec35a4f909423f85ed23340bf92371
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844351B1

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