Water → 3-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid

HRID 925269

반응식

HRID 925269 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[S:11][CH2:12][CH2:13][C:14]([F:23])([F:22])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[O:4].[OH-].[Na+].O>CCO>[F:23][C:14]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:13][CH2:12][S:11][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:5]=1[C:3]([OH:4])=[O:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 867201653-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester

생성물 1

HCID 867201663-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid수율 83.3%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

To a solution of 3-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester (0.33 g, 0.96 mmol) in EtOH (10 ml) are added sodium hydroxide (0.15 g, 3.87 mmol) and water (10 ml). The reaction mixture is stirred at 80° C. for 1 h. After completion of the reaction, the solvent is evaporated and the residue is diluted with water (10 ml). The aqueous layer is acidified with 2M hydrochloric acid to pH 3 and extracted with EtOAc (3×20 ml). The combined organic layers are washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude 3-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid (0.26 g, 0.8 mmol, 82%), which is used in the next step without further purification.

후처리

  1. customAfter completion of the reaction
  2. customthe solvent is evaporated
  3. additionthe residue is diluted with water (10 ml)
  4. extractionextracted with EtOAc (3×20 ml)
  5. washThe combined organic layers are washed with water (20 ml), brine (20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

출처 및 근거

ORD 기록
ord-d6a583cd36e34a19a84921fd10b457b6
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284286B2

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