Lithium Hydroxide → [3-(2-Benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid

HRID 1944401

반응식

HRID 1944401 반응식
C[O:2][C:3](=[O:32])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[C:17]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:6]1[CH3:31].[OH-].[Li+]>O1CCCC1>[C:25]1([S:22]([C:17]2[C:16]([CH2:15][C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=4)[N:5]([CH2:4][C:3]([OH:32])=[O:2])[C:6]=3[CH3:31])=[CH:21][CH:20]=[CH:19][N:18]=2)(=[O:24])=[O:23])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 67044945[3-(2-Benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

생성물 1

HCID 59380586[3-(2-Benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid수율 70.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of [3-(2-benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.16 g) and tetrahydrofuran (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.5 mL), and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was concentrated under reduced pressure, pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (5:95 to 98:2 by volume) to afford the title compound as a white solid (0.11 g).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionpH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative reverse-phase HPLC
  9. washeluting with a mixture of acetonitrile and water (5:95 to 98:2 by volume)

출처 및 근거

ORD 기록
ord-34eaa9904c9c424c84bb5be4faa2ef1c
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394836B2

연결된 노트

불러오는 중…