Lithium Hydroxide → 2-(Difluoromethyl)-5-(isobutyramidomethyl)nicotinic acid

HRID 1469797ノート

反応式

HRID 1469797 の反応式
[F:1][CH:2]([F:21])[C:3]1[N:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:10][C:4]=1[C:5]([O:7]CC)=[O:6].[Li+].[OH-]>O1CCOCC1.O>[F:21][CH:2]([F:1])[C:3]1[N:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:10][C:4]=1[C:5]([OH:7])=[O:6]

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 71059744Ethyl 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinate

生成物 1

HCID 710598402-(Difluoromethyl)-5-(isobutyramidomethyl)nicotinic acid収率 83.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of ethyl 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinate (200 mg, 0.66 mmol) in 1,4-Dioxane was added a solution of LiOH (70 mg, 1.66 mmol) in H2O (1 mL) and the reaction mixture was stirred at rt for 1 h. Then the reaction mixture was quenched with 1N HCl and the precipitated solid was filtered and dried to afford 150 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 13.98 (br s, 1H), 8.72 (s, 1H), 8.45 (t, 1H), 8.17 (s, 1H), 7.67-7.32 (t, J=54 Hz, 1H), 4.39-4.37 (d, J=5.7 Hz, 2H), 2.43 (m, 1H), 1.04-1.02 (d, J=6.6 Hz, 6H).

後処理

  1. customThen the reaction mixture was quenched with 1N HCl
  2. filtrationthe precipitated solid was filtered
  3. customdried

出典と根拠

ORDレコード
ord-899338ff0e1a4ce2b13d6d88e2de94ca
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

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