Lithium hydroxide, monohydrate → 6-(((Tert-butoxy)carbonyl)(ethyl)amino)pyridine-3-carboxylic acid

HRID 1874068

反応式

HRID 1874068 の反応式
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH3:12])=[N:6][CH:5]=1.O.[OH-].[Li+]>O1CCOCC1.O>[C:16]([O:15][C:13]([N:10]([CH2:11][CH3:12])[C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:20])=[O:2])=[CH:5][N:6]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 667701426-(Tert-butoxycarbonyl-ethyl-amino)-nicotinic acid methyl ester

生成物 1

HCID 667695526-(((Tert-butoxy)carbonyl)(ethyl)amino)pyridine-3-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

The crude 6-(tert-butoxycarbonyl-ethyl-amino)-nicotinic acid methyl ester is taken up in 100 mL dioxane and a solution of lithium hydroxide monohydrate (13.5 g, 0.32 mol) in 100 mL water is added and the reaction mixture is stirred at RT for 4 h. The dioxane is removed from the reaction mixture under reduced pressure, water is added and the reaction mixture is acidified to pH 6 with a solution of 10% citric acid in water. The formed precipitate is filtered off and dried in vacuo. Yield: 36 g. 1H NMR (DMSO-d6): δ 13.2 (s, 1H), 8.8 (s, 1H), 8.2 (d, 1H), 7.8 (d, 1H), 4.0 (quart, 2H), 1.5 (s, 9H), 1.2 (t, 3H).

後処理

  1. customThe dioxane is removed from the reaction mixture under reduced pressure, water
  2. additionis added
  3. filtrationThe formed precipitate is filtered off
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-d0e12d01cb314f60a742f161c019c64b
出典データセット
uspto-grants-2012_11
特許番号
US08304556B2

関連ノート

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