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

HRID 469773

반응식

HRID 469773 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-e39dfebc7aa94f58bc09824be7b733a8
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629166B2

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