Hydrochloric Acid → 5-Cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinic acid

HRID 469773

反応式

HRID 469773 の反応式
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:7]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[N:6][CH:5]=1.C1COCC1.O.[OH-].[Li+].Cl>O>[CH:10]1([C:8]2[C:7]([O:16][CH2:17][C:18]([F:21])([F:19])[F:20])=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([OH:22])=[O:2])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 71294015Methyl 5-cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinate

生成物 1

HCID 712939525-Cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinic acid収率 101.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5-Cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinic acid methyl ester (95 mg, 299 μmol) was combined with THF (4 mL) and water (2 mL) to give a light yellow solution. Lithium hydroxide hydrate (25.1 mg, 599 μmol) was added under argon. The reaction mixture was stirred at ambient temperature over night; poured into 6 mL 2 M HCl solution and extracted with i-propyl acetate (2×60 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to give the title compound (92 mg, quant.) as white solid that was used in the subsequent reactions without further purification; MS (ESI) 302.0 (M−H)−.

後処理

  1. customto give a light yellow solution
  2. extractionextracted with i-propyl acetate (2×60 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e39dfebc7aa94f58bc09824be7b733a8
出典データセット
uspto-grants-2014_01
特許番号
US08629166B2

関連ノート

読み込み中…