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

HRID 1874068

반응식

HRID 1874068 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d0e12d01cb314f60a742f161c019c64b
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304556B2

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