Water → 6-{4-Chloro-3-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-nicotinic acid

HRID 1095955노트

반응식

HRID 1095955 반응식
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH:18]([CH3:32])[C:19]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([Cl:31])[CH:26]=3)([OH:24])[C:20]([F:23])([F:22])[F:21])[CH:12]=2)=[N:6][CH:5]=1.[Li+].[OH-].O>C1COCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:33])=[O:2])=[CH:5][N:6]=2)=[CH:12][C:13]=1[CH:18]([CH3:32])[C:19]([C:25]1[CH:30]=[CH:29][N:28]=[C:27]([Cl:31])[CH:26]=1)([OH:24])[C:20]([F:23])([F:21])[F:22]

참가 물질

5

반응물 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 723105956-{4-Chloro-3-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-nicotinic acid methyl ester

생성물 1

HCID 723105716-{4-Chloro-3-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-nicotinic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

6-{4-Chloro-3-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-nicotinic acid methyl ester (14 mg, obtained in Example 132) was dissolved in THF (5 mL). The mixture was cooled in an ice bath and aqueous LiOH solution (1.0 M, 0.048 mL) was added. The mixture was stirred over night at r.t. The reaction mixture was poured into water and extracted with ethyl acetate. The aqueous phase was acidified with 2 M aqueous HCl to pH 1 and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and the solvent was evaporated. The title compound was obtained as an off-white solid (12 mg, 88%) and was used without further purification. MS (neg. ion, m/e)=485.0 [(M−H)−].

후처리

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionextracted with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-258201d7d6904bb4bbcffa7fbd612d3a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138189B2

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